feat(places): enrich list-imported places via the Places API (#886) (#1161)

* feat(places): enrich list-imported places via the Places API (#886)

Google/Naver list imports only carry a name and coordinates, so the places open
as bare pins — the Maps tab jumps to coordinates, with no photo, address or
open/closed. Add an opt-in "Enrich places via Google" toggle to the list-import
dialog, shown only when a Google Maps key is configured.

When enabled, after the (fast, unchanged) import the server runs a background
pass that re-resolves each place by name — biased to and validated against the
imported coordinates so a common-name search cannot overwrite the wrong place —
and fills the empty address/website/phone/photo columns plus the resolved
google_place_id, pushing each row over the live sync. Opening hours and the
proper Maps link then work on demand from the stored id.

Enrichment only fills empty fields, runs detached so a long list never blocks
the import, and no-ops when no key is configured.

* fix(places): use the ToggleSwitch component for the enrich toggle

Match the rest of the app — the import-enrichment opt-in used a raw checkbox;
swap it for the shared ToggleSwitch (text left, switch right) like the settings
toggles.

client/src/api/client.ts

@@ -18,7 +18,7 @@ import {
   type TripAddMemberRequest, type AssignmentReorderRequest,
   type PackingReorderRequest, type PackingCreateBagRequest, type TodoReorderRequest,
   type TripCreateRequest, type TripUpdateRequest, type TripCopyRequest,
-  type DayCreateRequest, type DayUpdateRequest,
+  type DayCreateRequest, type DayUpdateRequest, type DayReorderRequest,
   type PlaceCreateRequest, type PlaceUpdateRequest,
   type ReservationCreateRequest, type ReservationUpdateRequest,
   type AccommodationCreateRequest, type AccommodationUpdateRequest,
@@ -341,6 +341,7 @@ export const daysApi = {
   create: (tripId: number | string, data: DayCreateRequest) => apiClient.post(`/trips/${tripId}/days`, data).then(r => r.data),
   update: (tripId: number | string, dayId: number | string, data: DayUpdateRequest) => apiClient.put(`/trips/${tripId}/days/${dayId}`, data).then(r => r.data),
   delete: (tripId: number | string, dayId: number | string) => apiClient.delete(`/trips/${tripId}/days/${dayId}`).then(r => r.data),
+  reorder: (tripId: number | string, orderedIds: number[]) => apiClient.put(`/trips/${tripId}/days/reorder`, { orderedIds } satisfies DayReorderRequest).then(r => r.data),
 }
 
 export const placesApi = {
@@ -365,10 +366,10 @@ export const placesApi = {
     if (opts?.paths !== undefined) fd.append('importPaths', String(opts.paths))
     return apiClient.post(`/trips/${tripId}/places/import/map`, fd, { headers: { 'Content-Type': 'multipart/form-data' } }).then(r => r.data)
   },
-  importGoogleList: (tripId: number | string, url: string) =>
-      apiClient.post(`/trips/${tripId}/places/import/google-list`, { url } satisfies PlaceImportListRequest).then(r => r.data),
-  importNaverList: (tripId: number | string, url: string) =>
-      apiClient.post(`/trips/${tripId}/places/import/naver-list`, { url }).then(r => r.data),
+  importGoogleList: (tripId: number | string, url: string, enrich?: boolean) =>
+      apiClient.post(`/trips/${tripId}/places/import/google-list`, { url, enrich } satisfies PlaceImportListRequest).then(r => r.data),
+  importNaverList: (tripId: number | string, url: string, enrich?: boolean) =>
+      apiClient.post(`/trips/${tripId}/places/import/naver-list`, { url, enrich } satisfies PlaceImportListRequest).then(r => r.data),
   bulkDelete: (tripId: number | string, ids: number[]) =>
       apiClient.post(`/trips/${tripId}/places/bulk-delete`, { ids } satisfies PlaceBulkDeleteRequest).then(r => r.data),
 }
@@ -486,6 +487,20 @@ export const addonsApi = {
   enabled: () => apiClient.get('/addons').then(r => r.data),
 }
 
+export const airtrailApi = {
+  getSettings: () => apiClient.get('/integrations/airtrail/settings').then(r => r.data),
+  saveSettings: (data: { url: string; apiKey?: string; allowInsecureTls?: boolean }) =>
+    apiClient.put('/integrations/airtrail/settings', data).then(r => r.data),
+  status: () => apiClient.get('/integrations/airtrail/status').then(r => r.data),
+  test: (data: { url?: string; apiKey?: string; allowInsecureTls?: boolean }) =>
+    apiClient.post('/integrations/airtrail/test', data).then(r => r.data),
+  sync: (): Promise<{ changed: number }> => apiClient.post('/integrations/airtrail/sync').then(r => r.data),
+  // flights + import are added with the trip-planner import (P2)
+  flights: () => apiClient.get('/integrations/airtrail/flights').then(r => r.data),
+  import: (tripId: number, flightIds: string[]) =>
+    apiClient.post(`/trips/${tripId}/reservations/import/airtrail`, { flightIds }).then(r => r.data),
+}
+
 export const journeyApi = {
   list: () => apiClient.get('/journeys').then(r => r.data),
   create: (data: JourneyCreateRequest) => apiClient.post('/journeys', data).then(r => r.data),
@@ -557,6 +572,11 @@ export const mapsApi = {
   placePhoto: (placeId: string, lat?: number, lng?: number, name?: string) => apiClient.get(`/maps/place-photo/${encodeURIComponent(placeId)}`, { params: { lat, lng, name } }).then(r => checkInDev(mapsPlacePhotoResultSchema, r.data, 'maps.placePhoto')),
   reverse: (lat: number, lng: number, lang?: string) => apiClient.get('/maps/reverse', { params: { lat, lng, lang } }).then(r => checkInDev(mapsReverseResultSchema, r.data, 'maps.reverse')),
   resolveUrl: (url: string) => apiClient.post('/maps/resolve-url', { url }).then(r => checkInDev(mapsResolveUrlResultSchema, r.data, 'maps.resolveUrl')),
+  // OSM-only POI explore: places of a category within the current map viewport bbox.
+  // Overpass can be slow on a fresh (uncached) area, so this call gets a longer
+  // timeout than the global default instead of aborting at 8s and showing nothing.
+  pois: (category: string, bbox: { south: number; west: number; north: number; east: number }, signal?: AbortSignal) =>
+    apiClient.get('/maps/pois', { params: { category, ...bbox }, signal, timeout: 20000 }).then(r => r.data as { pois: import('../components/Map/poiCategories').Poi[]; source: string; truncated: boolean; clamped?: boolean }),
 }
 
 export const airportsApi = {

client/src/components/Admin/AddonManager.tsx

@@ -4,10 +4,10 @@ import { useTranslation } from '../../i18n'
 import { useSettingsStore } from '../../store/settingsStore'
 import { useAddonStore } from '../../store/addonStore'
 import { useToast } from '../shared/Toast'
-import { Puzzle, ListChecks, Wallet, FileText, CalendarDays, Globe, Briefcase, Image, Terminal, Link2, Compass, BookOpen, MessageCircle, StickyNote, BarChart3, Sparkles, Luggage } from 'lucide-react'
+import { Puzzle, ListChecks, Wallet, FileText, CalendarDays, Globe, Briefcase, Image, Terminal, Link2, Compass, BookOpen, MessageCircle, StickyNote, BarChart3, Sparkles, Luggage, Plane } from 'lucide-react'
 
 const ICON_MAP = {
-  ListChecks, Wallet, FileText, CalendarDays, Puzzle, Globe, Briefcase, Image, Terminal, Link2, Compass, BookOpen,
+  ListChecks, Wallet, FileText, CalendarDays, Puzzle, Globe, Briefcase, Image, Terminal, Link2, Compass, BookOpen, Plane,
 }
 
 function ImmichIcon({ size = 14 }: { size?: number }) {

client/src/components/Admin/DefaultUserSettingsTab.tsx

@@ -22,8 +22,22 @@ type Defaults = {
   time_format?: string
   blur_booking_codes?: boolean
   map_tile_url?: string
+  map_provider?: string
+  mapbox_access_token?: string
+  mapbox_style?: string
+  mapbox_3d_enabled?: boolean
+  mapbox_quality_mode?: boolean
 }
 
+const MAPBOX_STYLE_PRESETS = [
+  { name: 'Standard', url: 'mapbox://styles/mapbox/standard' },
+  { name: 'Streets', url: 'mapbox://styles/mapbox/streets-v12' },
+  { name: 'Outdoors', url: 'mapbox://styles/mapbox/outdoors-v12' },
+  { name: 'Light', url: 'mapbox://styles/mapbox/light-v11' },
+  { name: 'Dark', url: 'mapbox://styles/mapbox/dark-v11' },
+  { name: 'Satellite Streets', url: 'mapbox://styles/mapbox/satellite-streets-v12' },
+]
+
 function OptionRow({
   label,
   hint,
@@ -77,11 +91,15 @@ export default function DefaultUserSettingsTab(): React.ReactElement {
   const [defaults, setDefaults] = useState<Defaults>({})
   const [loaded, setLoaded] = useState(false)
   const [mapTileUrl, setMapTileUrl] = useState('')
+  const [mapboxToken, setMapboxToken] = useState('')
+  const [mapboxStyle, setMapboxStyle] = useState('')
 
   useEffect(() => {
     adminApi.getDefaultUserSettings().then((data: Defaults) => {
       setDefaults(data)
       setMapTileUrl(data.map_tile_url || '')
+      setMapboxToken(data.mapbox_access_token || '')
+      setMapboxStyle(data.mapbox_style || '')
       setLoaded(true)
     }).catch(() => setLoaded(true))
   }, [])
@@ -101,6 +119,8 @@ export default function DefaultUserSettingsTab(): React.ReactElement {
       const updated = await adminApi.updateDefaultUserSettings({ [key]: null })
       setDefaults(updated)
       if (key === 'map_tile_url') setMapTileUrl('')
+      if (key === 'mapbox_access_token') setMapboxToken('')
+      if (key === 'mapbox_style') setMapboxStyle('')
       toast.success(t('admin.defaultSettings.reset'))
     } catch (err: unknown) {
       toast.error(err instanceof Error ? err.message : t('common.error'))
@@ -267,6 +287,94 @@ export default function DefaultUserSettingsTab(): React.ReactElement {
           })}
         </div>
       </div>
+
+      {/* ── Map provider / instance-wide Mapbox ───────────────────────── */}
+      <div style={{ borderTop: '1px solid var(--border-primary)', paddingTop: 20, marginTop: 4 }}>
+        <OptionRow
+          label={<>{t('admin.defaultSettings.mapProvider')} <ResetButton field="map_provider" /></>}
+          hint={t('admin.defaultSettings.mapProviderHint')}
+        >
+          {([
+            { value: 'leaflet', label: t('admin.defaultSettings.providerLeaflet') },
+            { value: 'mapbox-gl', label: t('admin.defaultSettings.providerMapbox') },
+          ] as const).map(opt => (
+            <OptionButton
+              key={opt.value}
+              active={(defaults.map_provider || 'leaflet') === opt.value}
+              onClick={() => save({ map_provider: opt.value })}
+            >
+              {opt.label}
+            </OptionButton>
+          ))}
+        </OptionRow>
+
+        {defaults.map_provider === 'mapbox-gl' && (
+          <div style={{ marginTop: 16, display: 'flex', flexDirection: 'column', gap: 18 }}>
+            <div>
+              <label className="block text-sm font-medium mb-1.5 text-content-secondary">
+                {t('admin.defaultSettings.mapboxToken')}
+                <ResetButton field="mapbox_access_token" />
+              </label>
+              <input
+                type="text"
+                value={mapboxToken}
+                onChange={(e: React.ChangeEvent<HTMLInputElement>) => setMapboxToken(e.target.value)}
+                onBlur={() => save({ mapbox_access_token: mapboxToken })}
+                placeholder="pk.eyJ…"
+                spellCheck={false}
+                autoComplete="off"
+                className="w-full px-3 py-2 border border-slate-300 rounded-lg text-sm focus:ring-2 focus:ring-slate-400 focus:border-transparent"
+              />
+              <p className="text-xs mt-1 text-content-faint">{t('admin.defaultSettings.mapboxTokenHint')}</p>
+            </div>
+
+            <div>
+              <label className="block text-sm font-medium mb-1.5 text-content-secondary">
+                {t('admin.defaultSettings.mapboxStyle')}
+                <ResetButton field="mapbox_style" />
+              </label>
+              <CustomSelect
+                value={mapboxStyle}
+                onChange={(value: string) => { if (value) { setMapboxStyle(value); save({ mapbox_style: value }) } }}
+                placeholder={t('admin.defaultSettings.mapboxStylePlaceholder')}
+                options={MAPBOX_STYLE_PRESETS.map(p => ({ value: p.url, label: p.name }))}
+                size="sm"
+                style={{ marginBottom: 8 }}
+              />
+              <input
+                type="text"
+                value={mapboxStyle}
+                onChange={(e: React.ChangeEvent<HTMLInputElement>) => setMapboxStyle(e.target.value)}
+                onBlur={() => save({ mapbox_style: mapboxStyle })}
+                placeholder="mapbox://styles/mapbox/standard"
+                className="w-full px-3 py-2 border border-slate-300 rounded-lg text-sm focus:ring-2 focus:ring-slate-400 focus:border-transparent"
+              />
+            </div>
+
+            <OptionRow label={<>{t('admin.defaultSettings.mapbox3d')} <ResetButton field="mapbox_3d_enabled" /></>}>
+              {([
+                { value: true, label: t('settings.on') || 'On' },
+                { value: false, label: t('settings.off') || 'Off' },
+              ] as const).map(opt => (
+                <OptionButton key={String(opt.value)} active={(defaults.mapbox_3d_enabled ?? true) === opt.value} onClick={() => save({ mapbox_3d_enabled: opt.value })}>
+                  {opt.label}
+                </OptionButton>
+              ))}
+            </OptionRow>
+
+            <OptionRow label={<>{t('admin.defaultSettings.mapboxQuality')} <ResetButton field="mapbox_quality_mode" /></>}>
+              {([
+                { value: true, label: t('settings.on') || 'On' },
+                { value: false, label: t('settings.off') || 'Off' },
+              ] as const).map(opt => (
+                <OptionButton key={String(opt.value)} active={(defaults.mapbox_quality_mode ?? false) === opt.value} onClick={() => save({ mapbox_quality_mode: opt.value })}>
+                  {opt.label}
+                </OptionButton>
+              ))}
+            </OptionRow>
+          </div>
+        )}
+      </div>
     </Section>
   )
 }

client/src/components/Map/MapCompassPill.tsx

@@ -0,0 +1,48 @@
+import { useEffect, useState } from 'react'
+import { Navigation } from 'lucide-react'
+import type mapboxgl from 'mapbox-gl'
+
+/**
+ * Round compass pill for the Mapbox planner map. The Mapbox map can be rotated and
+ * pitched, so this shows the current bearing (the arrow points to north) and snaps
+ * the camera back to north + flat on click. Rendered next to the POI "explore" pill
+ * (Mapbox only) and built as the SAME frosted shell (padding 4 around a 34px button)
+ * so its height and transparency match the POI pill exactly.
+ */
+export function MapCompassPill({ map }: { map: mapboxgl.Map }) {
+  const [bearing, setBearing] = useState(() => map.getBearing())
+
+  useEffect(() => {
+    const update = () => setBearing(map.getBearing())
+    update()
+    map.on('rotate', update)
+    return () => { map.off('rotate', update) }
+  }, [map])
+
+  return (
+    <div style={{
+      display: 'inline-flex', alignItems: 'center', padding: 4, borderRadius: 999, pointerEvents: 'auto',
+      background: 'var(--sidebar-bg)',
+      backdropFilter: 'blur(20px) saturate(180%)',
+      WebkitBackdropFilter: 'blur(20px) saturate(180%)',
+      boxShadow: 'var(--sidebar-shadow, 0 4px 16px rgba(0,0,0,0.14))',
+    }}>
+      <button
+        type="button"
+        onClick={() => map.easeTo({ bearing: 0, pitch: 0, duration: 300 })}
+        aria-label="Reset north"
+        className="text-content-muted"
+        style={{
+          display: 'inline-flex', alignItems: 'center', justifyContent: 'center',
+          width: 34, height: 34, borderRadius: 999, border: 'none', cursor: 'pointer',
+          background: 'transparent', padding: 0,
+          transition: 'background 0.14s, color 0.14s',
+        }}
+        onMouseEnter={e => { e.currentTarget.style.background = 'var(--bg-hover)' }}
+        onMouseLeave={e => { e.currentTarget.style.background = 'transparent' }}
+      >
+        <Navigation size={16} strokeWidth={2} style={{ transform: `rotate(${-bearing}deg)`, transition: 'transform 0.1s linear' }} />
+      </button>
+    </div>
+  )
+}

client/src/components/Map/MapView.tsx

@@ -1,7 +1,7 @@
 import { useEffect, useRef, useState, useMemo, useCallback, createElement, memo } from 'react'
 import DOM from 'react-dom'
 import { renderToStaticMarkup } from 'react-dom/server'
-import { MapContainer, TileLayer, Marker, Polyline, CircleMarker, Circle, useMap } from 'react-leaflet'
+import { MapContainer, TileLayer, Marker, Polyline, CircleMarker, Circle, useMap, Tooltip } from 'react-leaflet'
 import MarkerClusterGroup from 'react-leaflet-cluster'
 import L from 'leaflet'
 import 'leaflet.markercluster/dist/MarkerCluster.css'
@@ -10,6 +10,7 @@ import { mapsApi } from '../../api/client'
 import { getCategoryIcon, CATEGORY_ICON_MAP } from '../shared/categoryIcons'
 import ReservationOverlay from './ReservationOverlay'
 import type { Reservation } from '../../types'
+import { POI_CATEGORY_BY_KEY, type Poi } from './poiCategories'
 
 function categoryIconSvg(iconName: string | null | undefined, size: number): string {
   const IconComponent = (iconName && CATEGORY_ICON_MAP[iconName]) || CATEGORY_ICON_MAP['MapPin']
@@ -118,6 +119,44 @@ function createPlaceIcon(place, orderNumbers, isSelected) {
   return fallbackIcon
 }
 
+// Small coloured pin for an OSM "explore" POI — distinct from the photo-circle
+// markers of planned places; the colour matches its pill category.
+const poiIconCache = new Map<string, L.DivIcon>()
+function createPoiIcon(category: string) {
+  const cached = poiIconCache.get(category)
+  if (cached) return cached
+  const cat = POI_CATEGORY_BY_KEY[category]
+  const color = cat?.color || '#6b7280'
+  const svg = cat ? renderToStaticMarkup(createElement(cat.Icon, { size: 13, color: 'white', strokeWidth: 2.5 })) : ''
+  const icon = L.divIcon({
+    className: '',
+    html: `<div style="width:26px;height:26px;border-radius:50%;background:${color};border:2px solid white;box-shadow:0 1px 5px rgba(0,0,0,0.3);display:flex;align-items:center;justify-content:center;cursor:pointer;">${svg}</div>`,
+    iconSize: [26, 26],
+    iconAnchor: [13, 13],
+    tooltipAnchor: [0, -14],
+  })
+  poiIconCache.set(category, icon)
+  return icon
+}
+
+// Emits the current viewport bbox on pan/zoom so the POI-explore pill can fetch
+// OSM places for the visible area.
+function ViewportController({ onViewportChange }: { onViewportChange?: (b: { south: number; west: number; north: number; east: number }) => void }) {
+  const map = useMap()
+  useEffect(() => {
+    if (!onViewportChange) return
+    const emit = () => {
+      const b = map.getBounds()
+      onViewportChange({ south: b.getSouth(), west: b.getWest(), north: b.getNorth(), east: b.getEast() })
+    }
+    map.whenReady(emit) // ensure the first bbox is captured once the map is laid out
+    map.on('moveend', emit)
+    map.on('zoomend', emit)
+    return () => { map.off('moveend', emit); map.off('zoomend', emit) }
+  }, [map, onViewportChange])
+  return null
+}
+
 interface SelectionControllerProps {
   places: Place[]
   selectedPlaceId: number | null
@@ -367,7 +406,21 @@ export const MapView = memo(function MapView({
   showReservationStats = false,
   visibleConnectionIds = [] as number[],
   onReservationClick,
+  pois = [] as Poi[],
+  onPoiClick,
+  onViewportChange,
 }: any) {
+  const poiMarkers = useMemo(() => (pois as Poi[]).map((poi: Poi) => (
+    <Marker
+      key={`poi-${poi.osm_id}`}
+      position={[poi.lat, poi.lng]}
+      icon={createPoiIcon(poi.category)}
+      zIndexOffset={500}
+      eventHandlers={{ click: () => onPoiClick?.(poi) }}
+    >
+      <Tooltip direction="top" offset={[0, -10]} opacity={1} className="map-tooltip">{poi.name}</Tooltip>
+    </Marker>
+  )), [pois, onPoiClick])
   const visibleReservations = useMemo(() => {
     if (!visibleConnectionIds || visibleConnectionIds.length === 0) return []
     const set = new Set(visibleConnectionIds)
@@ -543,6 +596,7 @@ export const MapView = memo(function MapView({
       <SelectionController places={places} selectedPlaceId={selectedPlaceId} dayPlaces={dayPlaces} paddingOpts={paddingOpts} />
       <MapClickHandler onClick={onMapClick} />
       <MapContextMenuHandler onContextMenu={onMapContextMenu} />
+      <ViewportController onViewportChange={onViewportChange} />
       <LeafletLocationLayer position={userPosition} mode={trackingMode} />
 
       <MarkerClusterGroup
@@ -583,6 +637,8 @@ export const MapView = memo(function MapView({
         showStats={showReservationStats}
         onEndpointClick={onReservationClick}
       />
+
+      {poiMarkers}
     </MapContainer>
     {isMobile && <LocationButton
       mode={trackingMode}

client/src/components/Map/MapViewGL.test.tsx

@@ -40,6 +40,12 @@ vi.mock('mapbox-gl', () => ({
     })),
     LngLatBounds: vi.fn(() => ({ extend: vi.fn().mockReturnThis() })),
     NavigationControl: vi.fn(),
+    Popup: vi.fn(() => ({
+      setLngLat: vi.fn().mockReturnThis(),
+      setHTML: vi.fn().mockReturnThis(),
+      addTo: vi.fn().mockReturnThis(),
+      remove: vi.fn(),
+    })),
   },
 }))
 vi.mock('mapbox-gl/dist/mapbox-gl.css', () => ({}))

client/src/components/Map/MapViewGL.tsx

@@ -12,6 +12,8 @@ import { ReservationMapboxOverlay } from './reservationsMapbox'
 import LocationButton from './LocationButton'
 import { useGeolocation } from '../../hooks/useGeolocation'
 import type { Place, Reservation } from '../../types'
+import { POI_CATEGORY_BY_KEY, type Poi } from './poiCategories'
+import { buildPlacePopupHtml, buildPoiPopupHtml } from './placePopup'
 
 function categoryIconSvg(iconName: string | null | undefined, size: number): string {
   const IconComponent = (iconName && CATEGORY_ICON_MAP[iconName]) || CATEGORY_ICON_MAP['MapPin']
@@ -49,6 +51,10 @@ interface Props {
   visibleConnectionIds?: number[]
   showReservationStats?: boolean
   onReservationClick?: (reservationId: number) => void
+  pois?: Poi[]
+  onPoiClick?: (poi: Poi) => void
+  onViewportChange?: (bbox: { south: number; west: number; north: number; east: number }) => void
+  onMapReady?: (map: mapboxgl.Map | null) => void
 }
 
 function createMarkerElement(place: Place & { category_color?: string; category_icon?: string }, photoUrl: string | null, orderNumbers: number[] | null, selected: boolean): HTMLDivElement {
@@ -128,6 +134,17 @@ function createMarkerElement(place: Place & { category_color?: string; category_
   return wrap
 }
 
+// Small coloured pin for an OSM "explore" POI (matches the pill category colour).
+function createPoiMarkerElement(category: string): HTMLDivElement {
+  const cat = POI_CATEGORY_BY_KEY[category]
+  const color = cat?.color || '#6b7280'
+  const svg = cat ? renderToStaticMarkup(createElement(cat.Icon, { size: 13, color: 'white', strokeWidth: 2.5 })) : ''
+  const el = document.createElement('div')
+  el.style.cssText = 'width:26px;height:26px;cursor:pointer;'
+  el.innerHTML = `<div style="width:26px;height:26px;border-radius:50%;background:${color};border:2px solid #fff;box-shadow:0 1px 5px rgba(0,0,0,0.3);display:flex;align-items:center;justify-content:center;box-sizing:border-box;">${svg}</div>`
+  return el
+}
+
 export function MapViewGL({
   places = [],
   dayPlaces = [],
@@ -149,6 +166,10 @@ export function MapViewGL({
   visibleConnectionIds = [],
   showReservationStats = false,
   onReservationClick,
+  pois = [],
+  onPoiClick,
+  onViewportChange,
+  onMapReady,
 }: Props) {
   const mapboxStyle = useSettingsStore(s => s.settings.mapbox_style || 'mapbox://styles/mapbox/standard')
   const mapboxToken = useSettingsStore(s => s.settings.mapbox_access_token || '')
@@ -167,6 +188,16 @@ export function MapViewGL({
   // options without forcing a full overlay rebuild on every prop change.
   const onReservationClickRef = useRef(onReservationClick)
   onReservationClickRef.current = onReservationClick
+  const poiMarkersRef = useRef<mapboxgl.Marker[]>([])
+  // Single reusable hover popup (name/category/address card) shared by planned
+  // places and POI markers — mirrors the Leaflet map's hover tooltip.
+  const popupRef = useRef<mapboxgl.Popup | null>(null)
+  const onPoiClickRef = useRef(onPoiClick)
+  onPoiClickRef.current = onPoiClick
+  const onViewportChangeRef = useRef(onViewportChange)
+  onViewportChangeRef.current = onViewportChange
+  const onMapReadyRef = useRef(onMapReady)
+  onMapReadyRef.current = onMapReady
   const { position: userPosition, mode: trackingMode, error: trackingError, cycleMode: cycleTrackingMode, setMode: setTrackingMode } = useGeolocation()
   const onClickRefs = useRef({ marker: onMarkerClick, map: onMapClick, context: onMapContextMenu })
   onClickRefs.current.marker = onMarkerClick
@@ -189,6 +220,16 @@ export function MapViewGL({
       projection: mapboxQuality ? 'globe' : 'mercator',
     })
     mapRef.current = map
+    popupRef.current = new mapboxgl.Popup({
+      closeButton: false,
+      closeOnClick: false,
+      offset: 18,
+      maxWidth: '240px',
+      className: 'trek-map-popup',
+    })
+    // Hand the map out so the trip planner can render its own compass pill next to
+    // the POI pill (a custom round control instead of Mapbox's default top-right one).
+    onMapReadyRef.current?.(map)
     // eslint-disable-next-line @typescript-eslint/no-explicit-any
     ;(window as any).__trek_map = map
 
@@ -260,6 +301,14 @@ export function MapViewGL({
       if (t.closest('.mapboxgl-marker')) return // markers handle their own click
       onClickRefs.current.map?.({ latlng: { lat: e.lngLat.lat, lng: e.lngLat.lng } })
     })
+    // Emit the viewport bbox (pan/zoom + once on first idle) so the POI-explore
+    // pill can fetch OSM places for the visible area.
+    const emitViewport = () => {
+      const b = map.getBounds()
+      onViewportChangeRef.current?.({ south: b.getSouth(), west: b.getWest(), north: b.getNorth(), east: b.getEast() })
+    }
+    map.on('moveend', emitViewport)
+    map.once('idle', emitViewport)
     // In the mapbox-gl map the right mouse button is reserved for the
     // built-in rotate/pitch gesture, so we bind the "add place" action
     // to the middle mouse button (button === 1) instead.
@@ -326,6 +375,8 @@ export function MapViewGL({
       canvas.removeEventListener('auxclick', onAuxClick)
       markersRef.current.forEach(m => m.remove())
       markersRef.current.clear()
+      if (popupRef.current) { popupRef.current.remove(); popupRef.current = null }
+      onMapReadyRef.current?.(null)
       if (reservationOverlayRef.current) {
         reservationOverlayRef.current.destroy()
         reservationOverlayRef.current = null
@@ -399,6 +450,10 @@ export function MapViewGL({
   useEffect(() => {
     const map = mapRef.current
     if (!map) return
+    // Markers are about to be rebuilt; drop any open hover popup first. A marker
+    // recreated under the pointer (e.g. when its photo streams in) never fires
+    // mouseleave, which would otherwise leave the popup orphaned on the map.
+    popupRef.current?.remove()
     const ids = new Set(places.map(p => p.id))
 
     markersRef.current.forEach((marker, id) => {
@@ -419,6 +474,12 @@ export function MapViewGL({
         ev.stopPropagation()
         onClickRefs.current.marker?.(place.id)
       })
+      el.addEventListener('mouseenter', () => {
+        popupRef.current?.setLngLat([place.lng, place.lat])
+          .setHTML(buildPlacePopupHtml(place as Place & { category_color?: string; category_icon?: string; category_name?: string }, photoUrl))
+          .addTo(map)
+      })
+      el.addEventListener('mouseleave', () => { popupRef.current?.remove() })
       // Recreate marker each time rather than patching internal state —
       // mapbox-gl's internal _element bookkeeping breaks under DOM swaps.
       const existing = markersRef.current.get(place.id)
@@ -435,6 +496,26 @@ export function MapViewGL({
     })
   }, [places, selectedPlaceId, dayOrderMap, photoUrls])
 
+  // Reconcile OSM "explore" POI markers (imperative, kept separate from the
+  // planned-place markers so they don't cluster or get confused with them).
+  useEffect(() => {
+    const map = mapRef.current
+    if (!map || !mapReady) return
+    popupRef.current?.remove() // same orphan-popup guard as the place markers
+    poiMarkersRef.current.forEach(m => m.remove())
+    poiMarkersRef.current = []
+    for (const poi of (pois as Poi[])) {
+      const el = createPoiMarkerElement(poi.category)
+      el.addEventListener('mouseenter', () => {
+        popupRef.current?.setLngLat([poi.lng, poi.lat]).setHTML(buildPoiPopupHtml(poi)).addTo(map)
+      })
+      el.addEventListener('mouseleave', () => { popupRef.current?.remove() })
+      el.addEventListener('click', (ev) => { ev.stopPropagation(); onPoiClickRef.current?.(poi) })
+      const m = new mapboxgl.Marker({ element: el, anchor: 'center' }).setLngLat([poi.lng, poi.lat]).addTo(map)
+      poiMarkersRef.current.push(m)
+    }
+  }, [pois, mapReady])
+
   // Update route geojson
   useEffect(() => {
     const map = mapRef.current

client/src/components/Map/PoiCategoryPill.tsx

@@ -0,0 +1,101 @@
+import { RotateCw, AlertTriangle } from 'lucide-react'
+import { useTranslation } from '../../i18n'
+import { Tooltip } from '../shared/Tooltip'
+import { POI_CATEGORIES } from './poiCategories'
+
+interface Props {
+  active: Set<string>
+  onToggle: (key: string) => void
+  loadingKeys?: Set<string>
+  /** categories whose last fetch failed → show a retry affordance */
+  errorKeys?: Set<string>
+  /** true when the map moved since the last search → offer "search this area" */
+  moved?: boolean
+  onSearchArea?: () => void
+}
+
+// Frosted, icon-only segmented control that floats over the map. Active segments
+// fill with the category colour (matching their markers); the label shows in a
+// custom tooltip on hover so the pill stays compact and never needs to scroll.
+export default function PoiCategoryPill({ active, onToggle, loadingKeys, errorKeys, moved, onSearchArea }: Props) {
+  const { t } = useTranslation()
+  const anyError = !!errorKeys && Array.from(active).some(k => errorKeys.has(k))
+
+  const frosted: React.CSSProperties = {
+    background: 'var(--sidebar-bg)',
+    backdropFilter: 'blur(20px) saturate(180%)',
+    WebkitBackdropFilter: 'blur(20px) saturate(180%)',
+    boxShadow: 'var(--sidebar-shadow, 0 4px 16px rgba(0,0,0,0.14))',
+  }
+
+  return (
+    <div style={{ display: 'flex', flexDirection: 'column', alignItems: 'center', gap: 8 }}>
+      <div style={{ display: 'inline-flex', alignItems: 'center', gap: 2, padding: 4, borderRadius: 999, pointerEvents: 'auto', ...frosted }}>
+        {POI_CATEGORIES.map(cat => {
+          const on = active.has(cat.key)
+          const loading = loadingKeys?.has(cat.key)
+          return (
+            <Tooltip key={cat.key} label={t(cat.labelKey)} placement="bottom">
+              <button
+                type="button"
+                onClick={() => onToggle(cat.key)}
+                aria-pressed={on}
+                aria-label={t(cat.labelKey)}
+                className={on ? '' : 'text-content-muted'}
+                style={{
+                  position: 'relative',
+                  display: 'inline-flex', alignItems: 'center', justifyContent: 'center',
+                  width: 34, height: 34, borderRadius: 999, border: 'none', cursor: 'pointer',
+                  background: on ? cat.color : 'transparent',
+                  color: on ? '#fff' : undefined,
+                  transition: 'background 0.14s, color 0.14s',
+                }}
+                onMouseEnter={e => { if (!on) e.currentTarget.style.background = 'var(--bg-hover)' }}
+                onMouseLeave={e => { if (!on) e.currentTarget.style.background = 'transparent' }}
+              >
+                {loading ? (
+                  <span
+                    className="animate-spin"
+                    style={{
+                      width: 14, height: 14, borderRadius: 999, display: 'inline-block',
+                      border: '2px solid', borderColor: on ? 'rgba(255,255,255,0.45)' : 'var(--border-primary)',
+                      borderTopColor: on ? '#fff' : 'var(--text-muted)',
+                    }}
+                  />
+                ) : (
+                  <cat.Icon size={16} strokeWidth={2} />
+                )}
+                {on && !loading && errorKeys?.has(cat.key) && (
+                  <span style={{
+                    position: 'absolute', top: 2, right: 2, width: 8, height: 8,
+                    borderRadius: 999, background: '#ef4444', border: '1.5px solid var(--sidebar-bg)',
+                  }} />
+                )}
+              </button>
+            </Tooltip>
+          )
+        })}
+      </div>
+
+      {(moved || anyError) && active.size > 0 && (
+        <button
+          type="button"
+          onClick={onSearchArea}
+          className="text-content"
+          style={{
+            display: 'inline-flex', alignItems: 'center', gap: 6,
+            padding: '6px 13px', borderRadius: 999, border: 'none', cursor: 'pointer',
+            fontSize: 12, fontWeight: 600, fontFamily: 'inherit', pointerEvents: 'auto',
+            color: anyError ? '#ef4444' : undefined,
+            ...frosted,
+          }}
+        >
+          {anyError
+            ? <AlertTriangle size={13} strokeWidth={2.4} />
+            : <RotateCw size={13} strokeWidth={2.4} />}
+          {t('poi.searchThisArea')}
+        </button>
+      )}
+    </div>
+  )
+}

client/src/components/Map/ReservationOverlay.tsx

@@ -158,6 +158,7 @@ interface TransportItem {
   res: Reservation
   from: ReservationEndpoint
   to: ReservationEndpoint
+  waypoints: ReservationEndpoint[]
   type: TransportType
   arcs: [number, number][][]
   primaryArc: [number, number][]
@@ -353,15 +354,29 @@ export default function ReservationOverlay({ reservations, showConnections, show
     const out: TransportItem[] = []
     for (const r of reservations) {
       if (!TRANSPORT_TYPES.includes(r.type as TransportType)) continue
-      const eps = r.endpoints || []
-      const from = eps.find(e => e.role === 'from')
-      const to = eps.find(e => e.role === 'to')
-      if (!from || !to) continue
+      // Ordered waypoints (from · stops · to). A single-leg booking has exactly two,
+      // so the arc + markers below are byte-identical to before for it.
+      const waypoints = (r.endpoints || [])
+        .filter(e => e.role === 'from' || e.role === 'to' || e.role === 'stop')
+        .slice()
+        .sort((a, b) => (a.sequence ?? 0) - (b.sequence ?? 0))
+      if (waypoints.length < 2) continue
+      const from = waypoints[0]
+      const to = waypoints[waypoints.length - 1]
       const type = r.type as TransportType
       const isGeo = TYPE_META[type].geodesic
-      const arcs = isGeo
-        ? splitAntimeridian(greatCircle([from.lat, from.lng], [to.lat, to.lng]))
-        : [[[from.lat, from.lng], [to.lat, to.lng]] as [number, number][]]
+      // One arc per leg (between consecutive waypoints), concatenated.
+      const arcs: [number, number][][] = []
+      let distanceKm = 0
+      for (let i = 0; i < waypoints.length - 1; i++) {
+        const a = waypoints[i]
+        const b = waypoints[i + 1]
+        const segArcs = isGeo
+          ? splitAntimeridian(greatCircle([a.lat, a.lng], [b.lat, b.lng]))
+          : [[[a.lat, a.lng], [b.lat, b.lng]] as [number, number][]]
+        arcs.push(...segArcs)
+        distanceKm += haversineKm([a.lat, a.lng], [b.lat, b.lng])
+      }
       const primaryIdx = arcs.reduce((best, seg, idx, all) => seg.length > all[best].length ? idx : best, 0)
       const primaryArc = arcs[primaryIdx] ?? []
       const fallback: [number, number] = primaryArc.length > 0
@@ -369,12 +384,15 @@ export default function ReservationOverlay({ reservations, showConnections, show
         : [(from.lat + to.lat) / 2, (from.lng + to.lng) / 2]
 
       const duration = computeDuration(from, to, r.reservation_time || null, r.reservation_end_time || null)
-      const distance = `${Math.round(haversineKm([from.lat, from.lng], [to.lat, to.lng]))} km`
-      const mainLabel = from.code && to.code ? `${from.code} → ${to.code}` : null
+      const distance = `${Math.round(distanceKm)} km`
+      // Show the full route (FRA → BER → HND) when every waypoint has a code.
+      const mainLabel = waypoints.every(w => w.code)
+        ? waypoints.map(w => w.code).join(' → ')
+        : (from.code && to.code ? `${from.code} → ${to.code}` : null)
       const subParts = [duration, distance].filter(Boolean) as string[]
       const subLabel = subParts.length > 0 ? subParts.join(' · ') : null
 
-      out.push({ res: r, from, to, type, arcs, primaryArc, fallback, mainLabel, subLabel })
+      out.push({ res: r, from, to, waypoints, type, arcs, primaryArc, fallback, mainLabel, subLabel })
     }
     return out
   }, [reservations])
@@ -416,38 +434,21 @@ export default function ReservationOverlay({ reservations, showConnections, show
         />
       )))}
 
-      {visibleItems.flatMap(item => [
+      {visibleItems.flatMap(item => item.waypoints.map((wp, wi) => (
         <Marker
-          key={`from-${item.res.id}`}
-          position={[item.from.lat, item.from.lng]}
-          icon={endpointIcon(item.type, showEndpointLabels && labelVisibleIds.has(item.res.id) ? (item.from.code || cleanName(item.from.name)) : null)}
+          key={`wp-${item.res.id}-${wi}`}
+          position={[wp.lat, wp.lng]}
+          icon={endpointIcon(item.type, showEndpointLabels && labelVisibleIds.has(item.res.id) ? (wp.code || cleanName(wp.name)) : null)}
           pane={ENDPOINT_PANE}
           zIndexOffset={1000}
           eventHandlers={{ click: () => onEndpointClick?.(item.res.id) }}
         >
           <Tooltip direction="top" offset={[0, -8]} opacity={1} className="map-tooltip">
-            <div style={{ fontWeight: 600, fontSize: 12 }}>{item.from.name}</div>
+            <div style={{ fontWeight: 600, fontSize: 12 }}>{wp.name}</div>
             {item.res.title && <div className="text-content-muted" style={{ fontSize: 11 }}>{item.res.title}</div>}
           </Tooltip>
-        </Marker>,
-        <Marker
-          key={`to-${item.res.id}`}
-          position={[item.to.lat, item.to.lng]}
-          icon={endpointIcon(item.type, showEndpointLabels && labelVisibleIds.has(item.res.id) ? (item.to.code || cleanName(item.to.name)) : null)}
-          pane={ENDPOINT_PANE}
-          zIndexOffset={1000}
-          eventHandlers={{ click: () => onEndpointClick?.(item.res.id) }}
-        >
-          <Tooltip direction="top" offset={[0, -8]} opacity={1} className="map-tooltip">
-            <div style={{ fontWeight: 600, fontSize: 12 }}>{item.to.name}</div>
-            {item.res.title && <div className="text-content-muted" style={{ fontSize: 11 }}>{item.res.title}</div>}
-          </Tooltip>
-        </Marker>,
-      ])}
-
-      {showStats && visibleItems.map(item => item.type === 'flight' && (item.mainLabel || item.subLabel) && labelVisibleIds.has(item.res.id) && (
-        <StatsLabel key={`stats-${item.res.id}`} item={item} />
-      ))}
+        </Marker>
+      )))}
     </>
   )
 }

client/src/components/Map/placePopup.ts

@@ -0,0 +1,68 @@
+import { createElement } from 'react'
+import { renderToStaticMarkup } from 'react-dom/server'
+import { CATEGORY_ICON_MAP } from '../shared/categoryIcons'
+import { POI_CATEGORY_BY_KEY, type Poi } from './poiCategories'
+import type { Place } from '../../types'
+
+// HTML builders for the Mapbox GL hover popup. The Leaflet map already shows a
+// name/category/address card on hover (a cursor-following overlay); Mapbox GL has
+// no equivalent, so these produce the same card as an HTML string for a
+// mapboxgl.Popup. Kept framework-agnostic (plain strings) on purpose.
+
+type PlaceWithCategory = Place & {
+  category_color?: string | null
+  category_icon?: string | null
+  category_name?: string | null
+}
+
+function esc(s: string | null | undefined): string {
+  if (!s) return ''
+  return String(s)
+    .replace(/&/g, '&')
+    .replace(/</g, '&lt;')
+    .replace(/>/g, '&gt;')
+    .replace(/"/g, '&quot;')
+}
+
+// Render a lucide category icon to an inline SVG string in the given colour.
+function iconSvg(iconName: string | null | undefined, size: number, color: string): string {
+  const Icon = (iconName && CATEGORY_ICON_MAP[iconName]) || CATEGORY_ICON_MAP['MapPin']
+  try {
+    return renderToStaticMarkup(createElement(Icon, { size, color, strokeWidth: 2 }))
+  } catch {
+    return ''
+  }
+}
+
+// Only data: thumbnails and our own photo-proxy URLs are safe to drop straight
+// into an <img src> — everything else is a fetch seed, not a displayable URL.
+function isDisplayablePhoto(url: string | null | undefined): url is string {
+  return !!url && (url.startsWith('data:') || url.startsWith('/api/maps/place-photo/'))
+}
+
+const CARD_OPEN = '<div style="font-family:var(--font-system);max-width:220px;">'
+const NAME_STYLE = 'font-weight:600;font-size:12.5px;color:#111827;overflow:hidden;text-overflow:ellipsis;white-space:nowrap;'
+const ADDR_STYLE = 'font-size:11px;color:#9ca3af;margin-top:3px;overflow:hidden;text-overflow:ellipsis;white-space:nowrap;'
+
+/** Hover-popup card for a planned place: optional photo, name, category row, address. */
+export function buildPlacePopupHtml(place: PlaceWithCategory, photoUrl: string | null): string {
+  const img = isDisplayablePhoto(photoUrl)
+    ? `<div style="width:100%;height:84px;border-radius:8px;overflow:hidden;margin-bottom:6px;background:#f3f4f6;"><img src="${esc(photoUrl)}" style="width:100%;height:100%;object-fit:cover;display:block;" /></div>`
+    : ''
+  const category =
+    place.category_name && place.category_icon
+      ? `<div style="display:flex;align-items:center;gap:4px;margin-top:2px;">${iconSvg(place.category_icon, 11, place.category_color || '#6b7280')}<span style="font-size:11px;color:#6b7280;">${esc(place.category_name)}</span></div>`
+      : ''
+  const address = place.address ? `<div style="${ADDR_STYLE}">${esc(place.address)}</div>` : ''
+  return `${CARD_OPEN}${img}<div style="${NAME_STYLE}">${esc(place.name)}</div>${category}${address}</div>`
+}
+
+/** Hover-popup card for an OSM "explore" POI: category-coloured icon, name, address. */
+export function buildPoiPopupHtml(poi: Poi): string {
+  const cat = POI_CATEGORY_BY_KEY[poi.category]
+  const color = cat?.color || '#6b7280'
+  const icon = cat ? renderToStaticMarkup(createElement(cat.Icon, { size: 12, color, strokeWidth: 2 })) : ''
+  const head = `<div style="display:flex;align-items:center;gap:5px;"><span style="flex-shrink:0;display:inline-flex;line-height:0;">${icon}</span><span style="${NAME_STYLE}">${esc(poi.name)}</span></div>`
+  const address = poi.address ? `<div style="${ADDR_STYLE}">${esc(poi.address)}</div>` : ''
+  return `${CARD_OPEN}${head}${address}</div>`
+}

client/src/components/Map/poiCategories.ts

@@ -0,0 +1,43 @@
+import { Utensils, Coffee, Wine, BedDouble, Camera, Landmark, Trees, Ticket, type LucideIcon } from 'lucide-react'
+
+// The POI categories shown in the map "explore" pill. The `key` is the contract
+// with the server (CATEGORY_OSM_FILTERS in mapsService.ts) — the OSM tag mapping
+// lives there; label/icon/colour live here. `color` doubles as the active-pill
+// fill AND the marker colour, so the pill and the map agree visually.
+export interface PoiCategory {
+  key: string
+  labelKey: string
+  Icon: LucideIcon
+  color: string
+}
+
+export const POI_CATEGORIES: PoiCategory[] = [
+  { key: 'restaurant', labelKey: 'poi.cat.restaurants', Icon: Utensils, color: '#EF4444' },
+  { key: 'cafe', labelKey: 'poi.cat.cafes', Icon: Coffee, color: '#B45309' },
+  { key: 'bar', labelKey: 'poi.cat.bars', Icon: Wine, color: '#A855F7' },
+  { key: 'hotel', labelKey: 'poi.cat.hotels', Icon: BedDouble, color: '#2563EB' },
+  { key: 'sights', labelKey: 'poi.cat.sights', Icon: Camera, color: '#EC4899' },
+  { key: 'museum', labelKey: 'poi.cat.museums', Icon: Landmark, color: '#6366F1' },
+  { key: 'nature', labelKey: 'poi.cat.nature', Icon: Trees, color: '#16A34A' },
+  { key: 'activity', labelKey: 'poi.cat.activities', Icon: Ticket, color: '#F59E0B' },
+]
+
+export const POI_CATEGORY_BY_KEY: Record<string, PoiCategory> = Object.fromEntries(
+  POI_CATEGORIES.map(c => [c.key, c]),
+)
+
+// One POI result from /api/maps/pois (mirror of the server's OverpassPoi).
+export interface Poi {
+  osm_id: string
+  name: string
+  lat: number
+  lng: number
+  category: string
+  poi_type: string
+  address: string | null
+  website: string | null
+  phone: string | null
+  opening_hours: string | null
+  cuisine: string | null
+  source: 'openstreetmap'
+}

client/src/components/Map/reservationsMapbox.ts

@@ -126,6 +126,7 @@ interface TransportItem {
   res: Reservation
   from: ReservationEndpoint
   to: ReservationEndpoint
+  waypoints: ReservationEndpoint[]
   type: TransportType
   arcs: [number, number][][]
   primaryArc: [number, number][]
@@ -137,23 +138,38 @@ function buildItems(reservations: Reservation[]): TransportItem[] {
   const out: TransportItem[] = []
   for (const r of reservations) {
     if (!TRANSPORT_TYPES.includes(r.type as TransportType)) continue
-    const eps = r.endpoints || []
-    const from = eps.find(e => e.role === 'from')
-    const to = eps.find(e => e.role === 'to')
-    if (!from || !to) continue
+    // Ordered waypoints (from · stops · to); a single-leg booking has exactly two.
+    const waypoints = (r.endpoints || [])
+      .filter(e => e.role === 'from' || e.role === 'to' || e.role === 'stop')
+      .slice()
+      .sort((a, b) => (a.sequence ?? 0) - (b.sequence ?? 0))
+    if (waypoints.length < 2) continue
+    const from = waypoints[0]
+    const to = waypoints[waypoints.length - 1]
     const type = r.type as TransportType
     const isGeo = TYPE_META[type].geodesic
-    const arcs = isGeo
-      ? splitAntimeridian(greatCircle([from.lat, from.lng], [to.lat, to.lng]))
-      : [[[from.lat, from.lng], [to.lat, to.lng]] as [number, number][]]
+    // One arc per leg (between consecutive waypoints), concatenated.
+    const arcs: [number, number][][] = []
+    let distanceKm = 0
+    for (let i = 0; i < waypoints.length - 1; i++) {
+      const a = waypoints[i]
+      const b = waypoints[i + 1]
+      const segArcs = isGeo
+        ? splitAntimeridian(greatCircle([a.lat, a.lng], [b.lat, b.lng]))
+        : [[[a.lat, a.lng], [b.lat, b.lng]] as [number, number][]]
+      arcs.push(...segArcs)
+      distanceKm += haversineKm([a.lat, a.lng], [b.lat, b.lng])
+    }
     const primaryIdx = arcs.reduce((best, seg, idx, all) => seg.length > all[best].length ? idx : best, 0)
     const primaryArc = arcs[primaryIdx] ?? []
     const duration = computeDuration(from, to, r.reservation_time || null, r.reservation_end_time || null)
-    const distance = `${Math.round(haversineKm([from.lat, from.lng], [to.lat, to.lng]))} km`
-    const mainLabel = from.code && to.code ? `${from.code} → ${to.code}` : null
+    const distance = `${Math.round(distanceKm)} km`
+    const mainLabel = waypoints.every(w => w.code)
+      ? waypoints.map(w => w.code).join(' → ')
+      : (from.code && to.code ? `${from.code} → ${to.code}` : null)
     const subParts = [duration, distance].filter(Boolean) as string[]
     const subLabel = subParts.length > 0 ? subParts.join(' · ') : null
-    out.push({ res: r, from, to, type, arcs, primaryArc, mainLabel, subLabel })
+    out.push({ res: r, from, to, waypoints, type, arcs, primaryArc, mainLabel, subLabel })
   }
   return out
 }
@@ -321,7 +337,7 @@ export class ReservationMapboxOverlay {
     if (show) {
       for (const item of visibleItems) {
         const showLabel = this.opts.showEndpointLabels && labelVisibleIds.has(item.res.id)
-        for (const ep of [item.from, item.to]) {
+        for (const ep of item.waypoints) {
           const label = showLabel ? (ep.code || cleanName(ep.name)) : null
           const el = document.createElement('div')
           el.innerHTML = endpointMarkerHtml(item.type, label)
@@ -342,29 +358,10 @@ export class ReservationMapboxOverlay {
       }
     }
 
-    // ── stats label (flights only) ──────────────────────────────────
+    // Stats badge removed — the floating route/duration label on the arc is no
+    // longer drawn; only the connection line and the airport markers remain.
     this.statsMarkers.forEach(s => s.marker.remove())
     this.statsMarkers = []
-    if (show && this.opts.showStats) {
-      for (const item of visibleItems) {
-        if (item.type !== 'flight') continue
-        if (!labelVisibleIds.has(item.res.id)) continue
-        if (!item.mainLabel && !item.subLabel) continue
-        const arc = item.primaryArc
-        if (arc.length < 2) continue
-        const mid = arc[Math.floor(arc.length / 2)]!
-        const { html, width, height } = buildStatsHtml(item.mainLabel, item.subLabel)
-        const el = document.createElement('div')
-        el.style.cssText = `width:${width}px;height:${height}px;pointer-events:none;`
-        el.innerHTML = html
-        const marker = new mapboxgl.Marker({ element: el, anchor: 'center' })
-          .setLngLat([mid[1], mid[0]])
-          .addTo(map)
-        this.statsMarkers.push({ marker, arc })
-      }
-    }
-    // Prime rotation once so labels don't flash horizontal on first paint.
-    this.updateStatsRotation()
   }
 
   // Match the Leaflet overlay's "rotate the label along the arc" look.

client/src/components/Map/usePoiExplore.ts

@@ -0,0 +1,115 @@
+import { useState, useRef, useCallback, useMemo } from 'react'
+import { mapsApi } from '../../api/client'
+import type { Poi } from './poiCategories'
+
+export interface Bbox { south: number; west: number; north: number; east: number }
+
+// A request we cancelled on purpose (newer search superseded it) — not a failure.
+function isAbortError(err: unknown): boolean {
+  const e = err as { name?: string; code?: string } | null
+  return e?.name === 'CanceledError' || e?.code === 'ERR_CANCELED' || e?.name === 'AbortError'
+}
+
+/**
+ * State for the map POI "explore" pill. Toggling a category fetches its OSM POIs
+ * for the current viewport; panning/zooming does NOT auto-refetch — it just marks
+ * the results stale (`moved`) so the pill can offer "search this area". This keeps
+ * Overpass load (and visual churn) down.
+ */
+export function usePoiExplore() {
+  const [active, setActive] = useState<Set<string>>(() => new Set())
+  const [byCat, setByCat] = useState<Record<string, Poi[]>>({})
+  const [loadingKeys, setLoadingKeys] = useState<Set<string>>(() => new Set())
+  const [moved, setMoved] = useState(false)
+  // Categories whose last fetch genuinely failed (all Overpass mirrors down), so
+  // the pill can offer a retry instead of looking like "no places here".
+  const [errorKeys, setErrorKeys] = useState<Set<string>>(() => new Set())
+
+  const bboxRef = useRef<Bbox | null>(null)
+  // activeRef always mirrors the latest active set so async callbacks (fetch
+  // completions) can check whether a category is still wanted.
+  const activeRef = useRef(active)
+  activeRef.current = active
+  // One in-flight AbortController per category, so re-toggling / re-searching
+  // cancels the previous (possibly slow) Overpass request instead of racing it.
+  const abortRef = useRef<Record<string, AbortController>>({})
+
+  const setLoading = useCallback((key: string, on: boolean) => setLoadingKeys(prev => {
+    const next = new Set(prev)
+    if (on) next.add(key); else next.delete(key)
+    return next
+  }), [])
+
+  const setError = useCallback((key: string, on: boolean) => setErrorKeys(prev => {
+    if (on === prev.has(key)) return prev
+    const next = new Set(prev)
+    if (on) next.add(key); else next.delete(key)
+    return next
+  }), [])
+
+  const fetchCat = useCallback(async (key: string, bbox: Bbox) => {
+    abortRef.current[key]?.abort()
+    const ctrl = new AbortController()
+    abortRef.current[key] = ctrl
+    setLoading(key, true)
+    setError(key, false)
+    try {
+      const res = await mapsApi.pois(key, bbox, ctrl.signal)
+      // Drop the result if the user toggled this category off while the (slow)
+      // Overpass request was in flight — otherwise stale results re-appear.
+      setByCat(prev => (activeRef.current.has(key) ? { ...prev, [key]: res.pois } : prev))
+    } catch (err) {
+      // A superseded request was aborted on purpose — leave its state untouched
+      // so the newer request owns the spinner and results.
+      if (isAbortError(err)) return
+      // A real failure (every Overpass mirror down/timed out): surface it instead
+      // of a silent empty so the user can retry rather than assume "no places".
+      setByCat(prev => (activeRef.current.has(key) ? { ...prev, [key]: [] } : prev))
+      if (activeRef.current.has(key)) setError(key, true)
+    } finally {
+      // Only the latest controller for this key clears the spinner; a superseded
+      // one must not, or it would hide the newer request's in-flight state.
+      if (abortRef.current[key] === ctrl) {
+        setLoading(key, false)
+        delete abortRef.current[key]
+      }
+    }
+  }, [setLoading, setError])
+
+  const onViewportChange = useCallback((bbox: Bbox) => {
+    bboxRef.current = bbox
+    if (activeRef.current.size > 0) setMoved(true)
+  }, [])
+
+  // Single-select: clicking a category switches to it (dropping the previous one
+  // and its markers immediately) and fetches it for the current viewport; clicking
+  // the already-active category turns it off.
+  const toggle = useCallback((key: string) => {
+    const isOnlyActive = activeRef.current.has(key) && activeRef.current.size === 1
+    setMoved(false)
+    setErrorKeys(new Set())
+    // Switching to another category (or turning off) — cancel any in-flight
+    // fetches so their results can't land after the selection changed.
+    Object.values(abortRef.current).forEach(c => c.abort())
+    abortRef.current = {}
+    if (isOnlyActive) {
+      setActive(new Set())
+      setByCat({})
+      return
+    }
+    setActive(new Set([key]))
+    setByCat({})
+    if (bboxRef.current) fetchCat(key, bboxRef.current)
+  }, [fetchCat])
+
+  const searchArea = useCallback(() => {
+    const bbox = bboxRef.current
+    if (!bbox) return
+    setMoved(false)
+    activeRef.current.forEach(key => fetchCat(key, bbox))
+  }, [fetchCat])
+
+  const pois = useMemo(() => Object.values(byCat).flat(), [byCat])
+
+  return { active, pois, loadingKeys, errorKeys, moved, toggle, searchArea, onViewportChange }
+}

client/src/components/PDF/TripPDF.tsx

@@ -215,7 +215,13 @@ export async function downloadTripPDF({ trip, days, places, assignments, categor
             const icon = reservationIconSvg(r.type)
             const color = RESERVATION_COLOR_MAP[r.type] || '#3b82f6'
             let subtitle = ''
-            if (r.type === 'flight') subtitle = [meta.airline, meta.flight_number, meta.departure_airport && meta.arrival_airport ? `${meta.departure_airport} → ${meta.arrival_airport}` : ''].filter(Boolean).join(' · ')
+            if (r.type === 'flight') {
+              // Full route over all waypoints (FRA → BER → HND), falling back to the
+              // flat metadata pair for legacy single-leg flights without endpoints.
+              const stops = (r.endpoints || []).slice().sort((a, b) => (a.sequence ?? 0) - (b.sequence ?? 0)).map(e => e.code || e.name)
+              const route = stops.length >= 2 ? stops.join(' → ') : (meta.departure_airport && meta.arrival_airport ? `${meta.departure_airport} → ${meta.arrival_airport}` : '')
+              subtitle = [meta.airline, meta.flight_number, route].filter(Boolean).join(' · ')
+            }
             else if (r.type === 'train') subtitle = [meta.train_number, meta.platform ? `Gl. ${meta.platform}` : '', meta.seat ? `Seat ${meta.seat}` : ''].filter(Boolean).join(' · ')
             else if (r.type === 'restaurant') subtitle = [meta.party_size ? `${meta.party_size} guests` : ''].filter(Boolean).join(' · ')
             else if (r.type === 'event') subtitle = [meta.venue].filter(Boolean).join(' · ')
@@ -287,6 +293,7 @@ export async function downloadTripPDF({ trip, days, places, assignments, categor
                   ${cat ? `<span class="cat-badge" style="background:${color}">${escHtml(cat.name)}</span>` : ''}
                 </div>
                 ${place.address ? `<div class="info-row">${svgPin}<span class="info-text">${escHtml(place.address)}</span></div>` : ''}
+                ${(place.lat != null && place.lng != null) ? `<div class="info-row"><span class="info-spacer"></span><span class="info-text muted">${Number(place.lat).toFixed(5)}, ${Number(place.lng).toFixed(5)}</span></div>` : ''}
                 ${place.description ? `<div class="info-row"><span class="info-spacer"></span><span class="info-text muted italic">${escHtml(place.description)}</span></div>` : ''}
                 ${chips ? `<div class="chips">${chips}</div>` : ''}
                 ${place.notes ? `<div class="info-row"><span class="info-spacer"></span><span class="info-text muted italic">${escHtml(place.notes)}</span></div>` : ''}

client/src/components/Packing/packingListPanel.constants.ts

@@ -45,7 +45,7 @@ export const KAT_COLORS = [
   '#14b8a6', // teal
 ]
 
-export const BAG_COLORS = ['#6366f1', '#ec4899', '#f97316', '#10b981', '#06b6d4', '#8b5cf6', '#ef4444', '#f59e0b']
+export const BAG_COLORS = ['#6366f1', '#ec4899', '#f97316', '#10b981', '#06b6d4', '#8b5cf6', '#ef4444', '#f59e0b', '#3b82f6', '#84cc16', '#d946ef', '#14b8a6', '#f43f5e', '#a855f7', '#eab308', '#64748b']
 
 // A category's first item is seeded with this sentinel because the server
 // rejects empty names. Treat it as a placeholder in the UI.

client/src/components/Planner/AirTrailImportModal.tsx

@@ -0,0 +1,261 @@
+import React from 'react'
+import ReactDOM from 'react-dom'
+import { useState, useRef, useEffect, useMemo } from 'react'
+import { Plane, X, Check } from 'lucide-react'
+import type { AirtrailFlight, AirtrailImportResult } from '@trek/shared'
+import { useTranslation } from '../../i18n'
+import { useToast } from '../shared/Toast'
+import { airtrailApi, reservationsApi } from '../../api/client'
+import { useTripStore } from '../../store/tripStore'
+
+interface AirTrailImportModalProps {
+  isOpen: boolean
+  onClose: () => void
+  tripId: number
+  pushUndo?: (label: string, undoFn: () => Promise<void> | void) => void
+}
+
+/** Locale-aware date (e.g. de → 13.06.2026, en-US → 06/13/2026). */
+function fmtDate(d: string | null, locale: string): string {
+  if (!d) return ''
+  try {
+    return new Date(d + 'T00:00:00Z').toLocaleDateString(locale, {
+      year: 'numeric',
+      month: '2-digit',
+      day: '2-digit',
+      timeZone: 'UTC',
+    })
+  } catch {
+    return d
+  }
+}
+
+export default function AirTrailImportModal({ isOpen, onClose, tripId, pushUndo }: AirTrailImportModalProps) {
+  const { t, locale } = useTranslation()
+  const toast = useToast()
+  const trip = useTripStore(s => s.trip)
+  const reservations = useTripStore(s => s.reservations)
+  const loadReservations = useTripStore(s => s.loadReservations)
+  const mouseDownTarget = useRef<EventTarget | null>(null)
+
+  const [loading, setLoading] = useState(false)
+  const [importing, setImporting] = useState(false)
+  const [error, setError] = useState('')
+  const [flights, setFlights] = useState<AirtrailFlight[]>([])
+  const [selected, setSelected] = useState<Set<string>>(() => new Set())
+
+  // AirTrail flight ids already linked to a reservation in this trip.
+  const importedIds = useMemo(() => {
+    const set = new Set<string>()
+    for (const r of reservations) {
+      if (r.external_source === 'airtrail' && r.external_id) set.add(String(r.external_id))
+    }
+    return set
+  }, [reservations])
+
+  const inRange = (f: AirtrailFlight): boolean =>
+    !!(f.date && trip?.start_date && trip?.end_date && f.date >= trip.start_date && f.date <= trip.end_date)
+
+  useEffect(() => {
+    if (!isOpen) return
+    setError('')
+    setSelected(new Set())
+    setLoading(true)
+    airtrailApi
+      .flights()
+      .then((d: { flights: AirtrailFlight[] }) => {
+        const list = d.flights ?? []
+        setFlights(list)
+        // Pre-select the flights that fall inside the trip and aren't imported yet.
+        const pre = new Set<string>()
+        for (const f of list) if (inRange(f) && !importedIds.has(f.id)) pre.add(f.id)
+        setSelected(pre)
+      })
+      .catch((err: any) => setError(err?.response?.data?.error ?? t('reservations.airtrail.loadError')))
+      .finally(() => setLoading(false))
+    // eslint-disable-next-line react-hooks/exhaustive-deps
+  }, [isOpen])
+
+  const { during, others } = useMemo(() => {
+    const during: AirtrailFlight[] = []
+    const others: AirtrailFlight[] = []
+    for (const f of flights) (inRange(f) ? during : others).push(f)
+    const byDateDesc = (a: AirtrailFlight, b: AirtrailFlight) => (b.date ?? '').localeCompare(a.date ?? '')
+    return { during: during.sort(byDateDesc), others: others.sort(byDateDesc) }
+    // eslint-disable-next-line react-hooks/exhaustive-deps
+  }, [flights, trip?.start_date, trip?.end_date])
+
+  const toggle = (id: string) => {
+    setSelected(prev => {
+      const next = new Set(prev)
+      if (next.has(id)) next.delete(id)
+      else next.add(id)
+      return next
+    })
+  }
+
+  const handleClose = () => { onClose() }
+
+  const handleImport = async () => {
+    const ids = [...selected].filter(id => !importedIds.has(id))
+    if (ids.length === 0 || importing) return
+    setImporting(true)
+    setError('')
+    try {
+      const result: AirtrailImportResult = await airtrailApi.import(tripId, ids)
+      await loadReservations(tripId)
+
+      const imported = result.imported ?? []
+      if (imported.length > 0) {
+        pushUndo?.(t('reservations.airtrail.undo'), async () => {
+          const linked = useTripStore.getState().reservations.filter(
+            r => r.external_source === 'airtrail' && r.external_id && imported.includes(String(r.external_id)),
+          )
+          await Promise.all(linked.map(r => reservationsApi.delete(tripId, r.id).catch(() => {})))
+          await loadReservations(tripId)
+        })
+        toast.success(t('reservations.airtrail.imported', { count: imported.length }))
+      }
+
+      const skippedInTrip = (result.skipped ?? []).filter(s => s.reason === 'already-in-trip').length
+      if (skippedInTrip > 0) toast.warning(t('reservations.airtrail.skippedDuplicate', { count: skippedInTrip }))
+      if (imported.length === 0 && skippedInTrip === 0) toast.warning(t('reservations.airtrail.nothingImported'))
+
+      handleClose()
+    } catch (err: any) {
+      setError(err?.response?.data?.error ?? t('reservations.airtrail.importError'))
+    } finally {
+      setImporting(false)
+    }
+  }
+
+  const selectableCount = [...selected].filter(id => !importedIds.has(id)).length
+
+  if (!isOpen) return null
+
+  const renderFlight = (f: AirtrailFlight) => {
+    const already = importedIds.has(f.id)
+    const isSelected = selected.has(f.id)
+    const label = f.flightNumber ? `${f.airline ? `${f.airline} ` : ''}${f.flightNumber}` : `${f.fromCode ?? '?'} → ${f.toCode ?? '?'}`
+    return (
+      <button
+        key={f.id}
+        onClick={() => !already && toggle(f.id)}
+        disabled={already}
+        className={already ? 'bg-surface-tertiary' : isSelected ? 'bg-surface-secondary' : 'bg-transparent'}
+        style={{
+          width: '100%', textAlign: 'left', borderRadius: 10, padding: '10px 12px', marginBottom: 8,
+          border: `1px solid ${isSelected && !already ? 'var(--accent)' : 'var(--border-primary)'}`,
+          opacity: already ? 0.55 : 1, cursor: already ? 'default' : 'pointer',
+          display: 'flex', gap: 10, alignItems: 'center', fontFamily: 'inherit',
+          transition: 'border-color 0.15s, background 0.15s',
+        }}
+      >
+        <span style={{
+          flexShrink: 0, width: 18, height: 18, borderRadius: 5,
+          border: `1.5px solid ${isSelected || already ? 'var(--accent)' : 'var(--border-primary)'}`,
+          background: isSelected || already ? 'var(--accent)' : 'transparent',
+          display: 'flex', alignItems: 'center', justifyContent: 'center',
+        }}>
+          {(isSelected || already) && <Check size={12} color="var(--accent-text)" strokeWidth={3} />}
+        </span>
+        <Plane size={15} color="#3b82f6" style={{ flexShrink: 0 }} />
+        <span style={{ flex: 1, minWidth: 0 }}>
+          <span style={{ display: 'block', fontSize: 13, fontWeight: 600, color: 'var(--text-primary)', overflow: 'hidden', textOverflow: 'ellipsis', whiteSpace: 'nowrap' }}>{label}</span>
+          <span style={{ display: 'block', fontSize: 11, color: 'var(--text-muted)' }}>
+            {f.fromCode ?? f.fromName ?? '?'} → {f.toCode ?? f.toName ?? '?'}{f.date ? ` · ${fmtDate(f.date, locale)}` : ''}
+          </span>
+        </span>
+        {already && (
+          <span style={{ flexShrink: 0, fontSize: 10, fontWeight: 600, color: 'var(--text-faint)' }}>
+            {t('reservations.airtrail.alreadyImported')}
+          </span>
+        )}
+      </button>
+    )
+  }
+
+  return ReactDOM.createPortal(
+    <div
+      className="bg-[rgba(0,0,0,0.4)]"
+      style={{ position: 'fixed', inset: 0, zIndex: 99999, display: 'flex', alignItems: 'center', justifyContent: 'center', padding: 16 }}
+      onMouseDown={e => { mouseDownTarget.current = e.target }}
+      onClick={e => {
+        if (e.target === e.currentTarget && mouseDownTarget.current === e.currentTarget) handleClose()
+        mouseDownTarget.current = null
+      }}
+    >
+      <div
+        onClick={e => e.stopPropagation()}
+        className="bg-surface-card"
+        style={{ borderRadius: 16, width: '100%', maxWidth: 540, padding: 24, boxShadow: '0 8px 32px rgba(0,0,0,0.2)', fontFamily: 'var(--font-system)', maxHeight: '90vh', display: 'flex', flexDirection: 'column' }}
+      >
+        <div style={{ display: 'flex', alignItems: 'center', gap: 8, marginBottom: 14 }}>
+          <Plane size={16} color="#3b82f6" />
+          <div style={{ flex: 1, fontSize: 15, fontWeight: 700, color: 'var(--text-primary)' }}>
+            {t('reservations.airtrail.title')}
+          </div>
+          <button onClick={handleClose} className="bg-transparent text-content-faint" style={{ border: 'none', cursor: 'pointer', padding: 4, borderRadius: 6, display: 'flex', alignItems: 'center' }}>
+            <X size={16} />
+          </button>
+        </div>
+
+        <div style={{ flex: 1, overflowY: 'auto', minHeight: 0 }}>
+          {loading && (
+            <div className="text-content-faint" style={{ fontSize: 13, textAlign: 'center', padding: '24px 0' }}>
+              {t('common.loading')}
+            </div>
+          )}
+
+          {!loading && flights.length === 0 && !error && (
+            <div className="text-content-faint" style={{ fontSize: 13, textAlign: 'center', padding: '24px 0' }}>
+              {t('reservations.airtrail.empty')}
+            </div>
+          )}
+
+          {!loading && during.length > 0 && (
+            <>
+              <div style={{ fontSize: 12, fontWeight: 700, color: 'var(--text-primary)', margin: '2px 0 8px' }}>
+                {t('reservations.airtrail.duringTrip')}
+              </div>
+              {during.map(renderFlight)}
+            </>
+          )}
+
+          {!loading && others.length > 0 && (
+            <>
+              <div style={{ fontSize: 12, fontWeight: 700, color: 'var(--text-faint)', margin: `${during.length > 0 ? 14 : 2}px 0 8px` }}>
+                {t('reservations.airtrail.otherFlights')}
+              </div>
+              {others.map(renderFlight)}
+            </>
+          )}
+
+          {error && (
+            <div className="bg-[rgba(239,68,68,0.08)] text-[#b91c1c]" style={{ border: '1px solid rgba(239,68,68,0.35)', borderRadius: 10, padding: '8px 10px', fontSize: 12, whiteSpace: 'pre-wrap', marginTop: 8 }}>
+              {error}
+            </div>
+          )}
+        </div>
+
+        <div style={{ display: 'flex', gap: 8, justifyContent: 'flex-end', marginTop: 14, paddingTop: 14, borderTop: '1px solid var(--border-faint)' }}>
+          <button
+            onClick={handleClose}
+            style={{ padding: '8px 16px', borderRadius: 10, border: '1px solid var(--border-primary)', background: 'none', color: 'var(--text-primary)', fontSize: 13, fontWeight: 500, cursor: 'pointer', fontFamily: 'inherit' }}
+          >
+            {t('common.cancel')}
+          </button>
+          <button
+            onClick={handleImport}
+            disabled={selectableCount === 0 || importing}
+            className={selectableCount > 0 && !importing ? 'bg-accent text-accent-text' : 'bg-surface-tertiary text-content-faint'}
+            style={{ padding: '8px 16px', borderRadius: 10, border: 'none', fontSize: 13, fontWeight: 500, cursor: selectableCount > 0 && !importing ? 'pointer' : 'default', fontFamily: 'inherit' }}
+          >
+            {importing ? t('common.loading') : t('reservations.airtrail.importCta', { count: selectableCount })}
+          </button>
+        </div>
+      </div>
+    </div>,
+    document.body,
+  )
+}

client/src/components/Planner/DayPlanSidebar.constants.ts

@@ -2,6 +2,7 @@ import {
   FileText, Info, Clock, MapPin, Navigation, Train, Plane, Bus, Car, Ship,
   Coffee, Ticket, Star, Heart, Camera, Flag, Lightbulb, AlertTriangle,
   ShoppingBag, Bookmark, Hotel, Utensils, Users, Sailboat, Bike, CarTaxiFront, Route,
+  Wine, ParkingSquare, Fuel, Footprints, Mountain, Waves, Sun, Umbrella, Music, Landmark, Gift,
 } from 'lucide-react'
 
 export const RES_ICONS = { flight: Plane, hotel: Hotel, restaurant: Utensils, train: Train, car: Car, cruise: Ship, bus: Bus, ferry: Sailboat, bicycle: Bike, taxi: CarTaxiFront, transport_other: Route, event: Ticket, tour: Users, other: FileText }
@@ -27,6 +28,18 @@ export const NOTE_ICONS = [
   { id: 'AlertTriangle', Icon: AlertTriangle },
   { id: 'ShoppingBag', Icon: ShoppingBag },
   { id: 'Bookmark', Icon: Bookmark },
+  { id: 'Utensils', Icon: Utensils },
+  { id: 'Wine', Icon: Wine },
+  { id: 'ParkingSquare', Icon: ParkingSquare },
+  { id: 'Fuel', Icon: Fuel },
+  { id: 'Footprints', Icon: Footprints },
+  { id: 'Mountain', Icon: Mountain },
+  { id: 'Waves', Icon: Waves },
+  { id: 'Sun', Icon: Sun },
+  { id: 'Umbrella', Icon: Umbrella },
+  { id: 'Music', Icon: Music },
+  { id: 'Landmark', Icon: Landmark },
+  { id: 'Gift', Icon: Gift },
 ]
 const NOTE_ICON_MAP = Object.fromEntries(NOTE_ICONS.map(({ id, Icon }) => [id, Icon]))
 export function getNoteIcon(iconId) { return NOTE_ICON_MAP[iconId] || FileText }

client/src/components/Planner/DayPlanSidebar.test.tsx

@@ -1708,4 +1708,49 @@ describe('DayPlanSidebar', () => {
     expect(onEditTransport).toHaveBeenCalledWith(res)
     expect(onEditReservation).not.toHaveBeenCalled()
   })
+
+  // ── showRouteToolsWhenExpanded (mobile route tools) ───────────────────────
+
+  it('FE-PLANNER-DAYPLAN-099: showRouteToolsWhenExpanded shows route tools on expanded day without selection', () => {
+    const places = [
+      buildPlace({ id: 1, name: 'A', lat: 48.85, lng: 2.35 }),
+      buildPlace({ id: 2, name: 'B', lat: 48.86, lng: 2.36 }),
+    ]
+    const day = buildDay({ id: 10, date: '2025-06-01', title: 'Day 1' })
+    const assigns = {
+      '10': [
+        buildAssignment({ id: 1, day_id: 10, order_index: 0, place: places[0] }),
+        buildAssignment({ id: 2, day_id: 10, order_index: 1, place: places[1] }),
+      ],
+    }
+    render(<DayPlanSidebar {...makeDefaultProps({
+      days: [day], places, assignments: assigns, selectedDayId: null, showRouteToolsWhenExpanded: true,
+    })} />)
+    // Days are expanded by default, so route tools must be visible even with no selected day
+    expect(screen.getByRole('button', { name: /optimize/i })).toBeInTheDocument()
+  })
+
+  it('FE-PLANNER-DAYPLAN-100: optimize via showRouteToolsWhenExpanded reorders the expanded day', async () => {
+    const user = userEvent.setup()
+    const onReorder = vi.fn().mockResolvedValue(undefined)
+    const places = [
+      buildPlace({ id: 1, name: 'A', lat: 48.85, lng: 2.35 }),
+      buildPlace({ id: 2, name: 'B', lat: 48.86, lng: 2.36 }),
+      buildPlace({ id: 3, name: 'C', lat: 48.87, lng: 2.37 }),
+    ]
+    const day = buildDay({ id: 10, date: '2025-06-01', title: 'Day 1' })
+    const assigns = {
+      '10': [
+        buildAssignment({ id: 1, day_id: 10, order_index: 0, place: places[0] }),
+        buildAssignment({ id: 2, day_id: 10, order_index: 1, place: places[1] }),
+        buildAssignment({ id: 3, day_id: 10, order_index: 2, place: places[2] }),
+      ],
+    }
+    render(<DayPlanSidebar {...makeDefaultProps({
+      days: [day], places, assignments: assigns, selectedDayId: null, onReorder, showRouteToolsWhenExpanded: true,
+    })} />)
+    const optimizeBtn = screen.getByRole('button', { name: /optimize/i })
+    await user.click(optimizeBtn)
+    await waitFor(() => expect(onReorder).toHaveBeenCalledWith(10, expect.any(Array)))
+  })
 })

client/src/components/Planner/DayPlanSidebar.tsx

@@ -51,6 +51,8 @@ interface DayPlanSidebarProps {
   onDayDetail: (day: Day) => void
   accommodations?: Accommodation[]
   onReorder: (dayId: number, orderedIds: number[]) => void
+  onReorderDays?: (orderedIds: number[]) => void
+  onAddDay?: (position?: number) => void
   onUpdateDayTitle: (dayId: number, title: string) => void
   onRouteCalculated: (route: RouteResult | null) => void
   onAssignToDay: (placeId: number, dayId: number, position?: number) => void
@@ -82,6 +84,8 @@ interface DayPlanSidebarProps {
   onAddBookingToAssignment?: (dayId: number, assignmentId: number) => void
   initialScrollTop?: number
   onScrollTopChange?: (top: number) => void
+  /** Mobile: show the route tools footer (Route toggle / Optimize / travel profile) on expanded days, since selecting a day closes the sheet */
+  showRouteToolsWhenExpanded?: boolean
 }
 
 /**
@@ -96,7 +100,7 @@ function useDayPlanSidebar(props: DayPlanSidebarProps) {
   trip, days, places, categories, assignments,
   selectedDayId, selectedPlaceId, selectedAssignmentId,
   onSelectDay, onPlaceClick, onDayDetail, accommodations = [],
-  onReorder, onUpdateDayTitle, onRouteCalculated,
+  onReorder, onReorderDays, onAddDay, onUpdateDayTitle, onRouteCalculated,
   onAssignToDay, onRemoveAssignment, onEditPlace, onDeletePlace,
   reservations = [],
   visibleConnectionIds = [],
@@ -123,6 +127,7 @@ function useDayPlanSidebar(props: DayPlanSidebarProps) {
   onAddBookingToAssignment,
   initialScrollTop,
   onScrollTopChange,
+  showRouteToolsWhenExpanded = false,
   } = props
   const toast = useToast()
   const { t, language, locale } = useTranslation()
@@ -171,7 +176,7 @@ function useDayPlanSidebar(props: DayPlanSidebarProps) {
   const [timeConfirm, setTimeConfirm] = useState<{
     dayId: number; fromId: number; time: string;
     // For drag & drop reorder
-    fromType?: string; toType?: string; toId?: number; insertAfter?: boolean;
+    fromType?: string; toType?: string; toId?: number; insertAfter?: boolean; toLegIndex?: number | null;
     // For arrow reorder
     reorderIds?: number[];
   } | null>(null)
@@ -376,14 +381,30 @@ function useDayPlanSidebar(props: DayPlanSidebarProps) {
     if (legsAbortRef.current) legsAbortRef.current.abort()
     if (!selectedDayId || !routeShown) { setRouteLegs({}); return }
     const merged = mergedItemsMap[selectedDayId] || []
+    const epLoc = (r: any, role: 'from' | 'to'): { lat: number; lng: number } | null => {
+      const e = (r.endpoints || []).find((x: any) => x.role === role)
+      return e && e.lat != null && e.lng != null ? { lat: e.lat, lng: e.lng } : null
+    }
     const runs: { id: number; lat: number; lng: number }[][] = []
     let cur: { id: number; lat: number; lng: number }[] = []
     for (const it of merged) {
       if (it.type === 'place' && it.data.place?.lat && it.data.place?.lng) {
         cur.push({ id: it.data.id, lat: it.data.place.lat, lng: it.data.place.lng })
       } else if (it.type === 'transport') {
-        if (cur.length >= 2) runs.push(cur)
-        cur = []
+        const r = it.data
+        const from = epLoc(r, 'from'), to = epLoc(r, 'to')
+        if (from || to) {
+          // Located transport: route to its departure point, break the run (the
+          // flight/train itself isn't driven), and let its arrival start the next.
+          if (from) cur.push({ id: r.id, lat: from.lat, lng: from.lng })
+          if (cur.length >= 2) runs.push(cur)
+          cur = []
+          if (to) cur.push({ id: r.id, lat: to.lat, lng: to.lng })
+        } else if (cur.length > 0) {
+          // No location: ignore for routing, but attribute the through-leg to the
+          // booking so its distance/duration shows under it (purely cosmetic).
+          cur[cur.length - 1] = { ...cur[cur.length - 1], id: r.id }
+        }
       }
     }
     if (cur.length >= 2) runs.push(cur)
@@ -471,6 +492,9 @@ function useDayPlanSidebar(props: DayPlanSidebarProps) {
     const assignmentIds: number[] = []
     const noteUpdates: { id: number; sort_order: number }[] = []
     const transportUpdates: { id: number; day_plan_position: number }[] = []
+    // Multi-leg flight legs share a reservation id, so their positions can't live in
+    // the single per-booking slot — collect them per leg, keyed reservationId → legIndex → pos.
+    const legPosUpdates: Record<number, Record<number, number>> = {}
 
     let placeCount = 0
     let i = 0
@@ -491,7 +515,10 @@ function useDayPlanSidebar(props: DayPlanSidebarProps) {
         group.forEach((g, idx) => {
           const pos = base + (idx + 1) / (group.length + 1)
           if (g.type === 'note') noteUpdates.push({ id: g.data.id, sort_order: pos })
-          else if (g.type === 'transport') transportUpdates.push({ id: g.data.id, day_plan_position: pos })
+          else if (g.type === 'transport') {
+            if (g.data.__leg) ((legPosUpdates[g.data.id] ??= {})[g.data.__leg.index] = pos)
+            else transportUpdates.push({ id: g.data.id, day_plan_position: pos })
+          }
         })
       }
     }
@@ -510,6 +537,30 @@ function useDayPlanSidebar(props: DayPlanSidebarProps) {
         }))
         setTransportPosVersion(v => v + 1)
       }
+      // Per-leg positions of multi-leg flights live in metadata.legs[i].day_positions
+      // (the single per-booking slot can't hold one position per leg).
+      const legResIds = Object.keys(legPosUpdates)
+      if (legResIds.length) {
+        for (const ridStr of legResIds) {
+          const rid = Number(ridStr)
+          const r = useTripStore.getState().reservations.find(x => x.id === rid)
+          if (!r) continue
+          let parsed: any = {}
+          try { parsed = typeof r.metadata === 'string' ? JSON.parse(r.metadata || '{}') : (r.metadata || {}) } catch { parsed = {} }
+          if (!Array.isArray(parsed.legs)) continue
+          const legs = parsed.legs.map((leg: any, i: number) => {
+            const pos = legPosUpdates[rid][i]
+            return pos == null ? leg : { ...leg, day_positions: { ...(leg.day_positions || {}), [dayId]: pos } }
+          })
+          // Send metadata as an OBJECT (like the form does) — passing a JSON string
+          // here double-encodes it on the server, which wipes metadata.legs on read
+          // and collapses the flight back to a single span.
+          const newMeta = { ...parsed, legs }
+          useTripStore.setState(state => ({ reservations: state.reservations.map(x => (x.id === rid ? { ...x, metadata: newMeta } : x)) }))
+          await tripActions.updateReservation(tripId, rid, { metadata: newMeta })
+        }
+        setTransportPosVersion(v => v + 1)
+      }
       if (assignmentIds.length) await onReorder(dayId, assignmentIds)
       if (transportUpdates.length) {
         onRouteRefresh?.()
@@ -528,8 +579,11 @@ function useDayPlanSidebar(props: DayPlanSidebarProps) {
     } catch (err: unknown) { toast.error(err instanceof Error ? err.message : t('common.unknownError')) }
   }
 
-  const handleMergedDrop = async (dayId, fromType, fromId, toType, toId, insertAfter = false) => {
+  const handleMergedDrop = async (dayId, fromType, fromId, toType, toId, insertAfter = false, toLegIndex = null) => {
     const m = getMergedItems(dayId)
+    // Multi-leg flights expose one item per leg sharing the same reservation id;
+    // disambiguate the drop target by leg index so you can drop BETWEEN legs.
+    const matchTo = (i: any) => i.type === toType && i.data.id === toId && (toLegIndex == null || i.data?.__leg?.index === toLegIndex)
 
     // Check if a timed place is being moved → would it break chronological order?
     if (fromType === 'place') {
@@ -537,11 +591,11 @@ function useDayPlanSidebar(props: DayPlanSidebarProps) {
       const fromMinutes = parseTimeToMinutes(fromItem?.data?.place?.place_time)
       if (fromItem && fromMinutes !== null) {
         const fromIdx = m.findIndex(i => i.type === fromType && i.data.id === fromId)
-        const toIdx = m.findIndex(i => i.type === toType && i.data.id === toId)
+        const toIdx = m.findIndex(matchTo)
         if (fromIdx !== -1 && toIdx !== -1) {
           const simulated = [...m]
           const [moved] = simulated.splice(fromIdx, 1)
-          let insertIdx = simulated.findIndex(i => i.type === toType && i.data.id === toId)
+          let insertIdx = simulated.findIndex(matchTo)
           if (insertIdx === -1) insertIdx = simulated.length
           if (insertAfter) insertIdx += 1
           simulated.splice(insertIdx, 0, moved)
@@ -558,7 +612,7 @@ function useDayPlanSidebar(props: DayPlanSidebarProps) {
           if (!isChronological) {
             const placeTime = fromItem.data.place.place_time
             const timeStr = placeTime.includes(':') ? placeTime.substring(0, 5) : placeTime
-            setTimeConfirm({ dayId, fromType, fromId, toType, toId, insertAfter, time: timeStr })
+            setTimeConfirm({ dayId, fromType, fromId, toType, toId, insertAfter, toLegIndex, time: timeStr })
             setDraggingId(null); setDropTargetKey(null); dragDataRef.current = null
             return
           }
@@ -568,7 +622,7 @@ function useDayPlanSidebar(props: DayPlanSidebarProps) {
 
     // Build new order: remove the dragged item, insert at target position
     const fromIdx = m.findIndex(i => i.type === fromType && i.data.id === fromId)
-    const toIdx = m.findIndex(i => i.type === toType && i.data.id === toId)
+    const toIdx = m.findIndex(matchTo)
     if (fromIdx === -1 || toIdx === -1 || fromIdx === toIdx) {
       setDraggingId(null); setDropTargetKey(null); dragDataRef.current = null
       return
@@ -576,7 +630,7 @@ function useDayPlanSidebar(props: DayPlanSidebarProps) {
 
     const newOrder = [...m]
     const [moved] = newOrder.splice(fromIdx, 1)
-    let adjustedTo = newOrder.findIndex(i => i.type === toType && i.data.id === toId)
+    let adjustedTo = newOrder.findIndex(matchTo)
     if (adjustedTo === -1) adjustedTo = newOrder.length
     if (insertAfter) adjustedTo += 1
     newOrder.splice(adjustedTo, 0, moved)
@@ -590,7 +644,7 @@ function useDayPlanSidebar(props: DayPlanSidebarProps) {
   const confirmTimeRemoval = async () => {
     if (!timeConfirm) return
     const saved = { ...timeConfirm }
-    const { dayId, fromId, reorderIds, fromType, toType, toId, insertAfter } = saved
+    const { dayId, fromId, reorderIds, fromType, toType, toId, insertAfter, toLegIndex } = saved
     setTimeConfirm(null)
 
     // Remove time from assignment
@@ -633,13 +687,14 @@ function useDayPlanSidebar(props: DayPlanSidebarProps) {
 
     // Drag & drop reorder
     if (fromType && toType) {
+      const matchTo = (i: any) => i.type === toType && i.data.id === toId && (toLegIndex == null || i.data?.__leg?.index === toLegIndex)
       const fromIdx = m.findIndex(i => i.type === fromType && i.data.id === fromId)
-      const toIdx = m.findIndex(i => i.type === toType && i.data.id === toId)
+      const toIdx = m.findIndex(matchTo)
       if (fromIdx === -1 || toIdx === -1 || fromIdx === toIdx) return
 
       const newOrder = [...m]
       const [moved] = newOrder.splice(fromIdx, 1)
-      let adjustedTo = newOrder.findIndex(i => i.type === toType && i.data.id === toId)
+      let adjustedTo = newOrder.findIndex(matchTo)
       if (adjustedTo === -1) adjustedTo = newOrder.length
       if (insertAfter) adjustedTo += 1
       newOrder.splice(adjustedTo, 0, moved)
@@ -690,18 +745,20 @@ function useDayPlanSidebar(props: DayPlanSidebarProps) {
     pushUndo?.(t('undo.lock'), () => { setLockedIds(prevLocked) })
   }
 
-  const handleOptimize = async () => {
-    if (!selectedDayId) return
-    const da = getDayAssignments(selectedDayId)
+  const handleOptimize = async (dayId: number | null = selectedDayId) => {
+    if (!dayId) return
+    const da = getDayAssignments(dayId)
     if (da.length < 3) return
 
     const prevIds = da.map(a => a.id)
 
-    // Separate locked (stay at their index) and unlocked assignments
+    // Separate fixed (stay at their index) and movable assignments. A place is
+    // fixed if it's locked OR has a set time — timed places are anchored by their
+    // time, so the optimizer must not reshuffle them.
     const locked = new Map() // index -> assignment
     const unlocked = []
     da.forEach((a, i) => {
-      if (lockedIds.has(a.id)) locked.set(i, a)
+      if (lockedIds.has(a.id) || a.place?.place_time) locked.set(i, a)
       else unlocked.push(a)
     })
 
@@ -710,7 +767,7 @@ function useDayPlanSidebar(props: DayPlanSidebarProps) {
     const unlockedNoCoords = unlocked.filter(a => !a.place?.lat || !a.place?.lng)
     // Anchor the route on the day's accommodation (when enabled): a loop out from and back to the
     // hotel, or — on a transfer day — a run from the hotel you leave to the one you arrive at.
-    const day = days.find(d => d.id === selectedDayId)
+    const day = days.find(d => d.id === dayId)
     const anchors = day && useSettingsStore.getState().settings.optimize_from_accommodation !== false
       ? getAccommodationAnchors(day, days, accommodations)
       : {}
@@ -727,10 +784,10 @@ function useDayPlanSidebar(props: DayPlanSidebarProps) {
       if (!result[i]) result[i] = optimizedQueue[qi++]
     }
 
-    await onReorder(selectedDayId, result.map(a => a.id))
+    await onReorder(dayId, result.map(a => a.id))
     const usedHotel = !!(anchors.start || anchors.end)
     toast.success(usedHotel ? t('dayplan.toast.routeOptimizedFromHotel') : t('dayplan.toast.routeOptimized'))
-    const capturedDayId = selectedDayId
+    const capturedDayId = dayId
     pushUndo?.(t('undo.optimize'), async () => {
       await tripActions.reorderAssignments(tripId, capturedDayId, prevIds)
     })
@@ -814,6 +871,8 @@ function useDayPlanSidebar(props: DayPlanSidebarProps) {
     onDayDetail,
     accommodations,
     onReorder,
+    onReorderDays,
+    onAddDay,
     onUpdateDayTitle,
     onRouteCalculated,
     onAssignToDay,
@@ -845,6 +904,7 @@ function useDayPlanSidebar(props: DayPlanSidebarProps) {
     onAddBookingToAssignment,
     initialScrollTop,
     onScrollTopChange,
+    showRouteToolsWhenExpanded,
     toast,
     t,
     language,
@@ -958,6 +1018,8 @@ const DayPlanSidebar = React.memo(function DayPlanSidebar(props: DayPlanSidebarP
     onDayDetail,
     accommodations,
     onReorder,
+    onReorderDays,
+    onAddDay,
     onUpdateDayTitle,
     onRouteCalculated,
     onAssignToDay,
@@ -989,6 +1051,7 @@ const DayPlanSidebar = React.memo(function DayPlanSidebar(props: DayPlanSidebarP
     onAddBookingToAssignment,
     initialScrollTop,
     onScrollTopChange,
+    showRouteToolsWhenExpanded,
     toast,
     t,
     language,
@@ -1109,6 +1172,9 @@ const DayPlanSidebar = React.memo(function DayPlanSidebar(props: DayPlanSidebarP
         undoHover={undoHover}
         setUndoHover={setUndoHover}
         lastActionLabel={lastActionLabel}
+        canEditDays={canEditDays}
+        onReorderDays={onReorderDays}
+        onAddDay={onAddDay}
       />
 
       {/* Tagesliste */}
@@ -1311,6 +1377,8 @@ const DayPlanSidebar = React.memo(function DayPlanSidebar(props: DayPlanSidebarP
                       const isAfter = dropTargetRef.current.startsWith('transport-after-')
                       const parts = dropTargetRef.current.replace('transport-after-', '').replace('transport-', '').split('-')
                       const transportId = Number(parts[0])
+                      const legPart = parts.find(p => /^leg\d+$/.test(p))
+                      const toLegIndex = legPart ? Number(legPart.slice(3)) : null
 
                       if (placeId) {
                         onAssignToDay?.(parseInt(placeId), day.id)
@@ -1318,15 +1386,15 @@ const DayPlanSidebar = React.memo(function DayPlanSidebar(props: DayPlanSidebarP
                         const r = reservations.find(x => x.id === Number(fromReservationId))
                         if (r) { const update = computeMultiDayMove(r, day.id, phase); tripActions.updateReservation(tripId, r.id, update).catch((err: unknown) => toast.error(err instanceof Error ? err.message : t('common.unknownError'))) }
                       } else if (fromReservationId) {
-                        handleMergedDrop(day.id, 'transport', Number(fromReservationId), 'transport', transportId, isAfter)
+                        handleMergedDrop(day.id, 'transport', Number(fromReservationId), 'transport', transportId, isAfter, toLegIndex)
                       } else if (assignmentId && fromDayId !== day.id) {
                         tripActions.moveAssignment(tripId, Number(assignmentId), fromDayId, day.id).catch((err: unknown) => toast.error(err instanceof Error ? err.message : t('common.unknownError')))
                       } else if (assignmentId) {
-                        handleMergedDrop(day.id, 'place', Number(assignmentId), 'transport', transportId, isAfter)
+                        handleMergedDrop(day.id, 'place', Number(assignmentId), 'transport', transportId, isAfter, toLegIndex)
                       } else if (noteId && fromDayId !== day.id) {
                         tripActions.moveDayNote(tripId, fromDayId, day.id, Number(noteId)).catch((err: unknown) => toast.error(err instanceof Error ? err.message : t('common.unknownError')))
                       } else if (noteId) {
-                        handleMergedDrop(day.id, 'note', Number(noteId), 'transport', transportId, isAfter)
+                        handleMergedDrop(day.id, 'note', Number(noteId), 'transport', transportId, isAfter, toLegIndex)
                       }
                       setDraggingId(null); setDropTargetKey(null); dragDataRef.current = null; window.__dragData = null
                       return
@@ -1372,9 +1440,10 @@ const DayPlanSidebar = React.memo(function DayPlanSidebar(props: DayPlanSidebarP
                     </div>
                   ) : (
                     merged.map((item, idx) => {
-                      const itemKey = item.type === 'transport' ? `transport-${item.data.id}-${day.id}` : (item.type === 'place' ? `place-${item.data.id}` : `note-${item.data.id}`)
+                      const legSuffix = item.data?.__leg ? `-leg${item.data.__leg.index}` : ''
+                      const itemKey = item.type === 'transport' ? `transport-${item.data.id}${legSuffix}-${day.id}` : (item.type === 'place' ? `place-${item.data.id}` : `note-${item.data.id}`)
                       const showDropLine = (!!draggingId || !!dropTargetKey) && dropTargetKey === itemKey
-                      const showDropLineAfter = item.type === 'transport' && (!!draggingId || !!dropTargetKey) && dropTargetKey === `transport-after-${item.data.id}-${day.id}`
+                      const showDropLineAfter = item.type === 'transport' && (!!draggingId || !!dropTargetKey) && dropTargetKey === `transport-after-${item.data.id}${legSuffix}-${day.id}`
 
                       if (item.type === 'place') {
                         const assignment = item.data
@@ -1722,7 +1791,13 @@ const DayPlanSidebar = React.memo(function DayPlanSidebar(props: DayPlanSidebarP
 
                         // Subtitle aus Metadaten zusammensetzen
                         let subtitle = ''
-                        if (res.type === 'flight') {
+                        if (res.__leg) {
+                          // One leg of a multi-leg flight — show this segment's own route.
+                          const parts = [res.__leg.airline, res.__leg.flight_number].filter(Boolean)
+                          if (res.__leg.from || res.__leg.to)
+                            parts.push([res.__leg.from, res.__leg.to].filter(Boolean).join(' → '))
+                          subtitle = parts.join(' · ')
+                        } else if (res.type === 'flight') {
                           const parts = [meta.airline, meta.flight_number].filter(Boolean)
                           if (meta.departure_airport || meta.arrival_airport)
                             parts.push([meta.departure_airport, meta.arrival_airport].filter(Boolean).join(' → '))
@@ -1731,28 +1806,32 @@ const DayPlanSidebar = React.memo(function DayPlanSidebar(props: DayPlanSidebarP
                           subtitle = [meta.train_number, meta.platform ? `Gl. ${meta.platform}` : '', meta.seat ? `Sitz ${meta.seat}` : ''].filter(Boolean).join(' · ')
                         }
 
-                        // Multi-day span phase
-                        const spanLabel = getSpanLabel(res, spanPhase)
+                        // Multi-day span phase (single-leg / non-flight only — a
+                        // multi-leg flight is shown as one row per leg, see below).
+                        const spanLabel = res.__leg ? null : getSpanLabel(res, spanPhase)
                         const displayTime = getDisplayTimeForDay(res, day.id)
+                        const legKey = res.__leg ? `leg${res.__leg.index}` : 'x'
 
                         return (
-                          <React.Fragment key={`transport-${res.id}-${day.id}`}>
+                          <React.Fragment key={`transport-${res.id}-${legKey}-${day.id}`}>
                           <div
                             onClick={() => {
                               if (!canEditDays) return
-                              if (TRANSPORT_TYPES.has(res.type)) onEditTransport?.(res)
-                              else onEditReservation?.(res)
+                              const target = reservations.find(x => x.id === res.id) ?? res
+                              if (TRANSPORT_TYPES.has(res.type)) onEditTransport?.(target)
+                              else onEditReservation?.(target)
                             }}
                             onDragOver={e => {
                               e.preventDefault(); e.stopPropagation()
                               const rect = e.currentTarget.getBoundingClientRect()
                               const inBottom = e.clientY > rect.top + rect.height / 2
-                              const key = inBottom ? `transport-after-${res.id}-${day.id}` : `transport-${res.id}-${day.id}`
+                              const ls = res.__leg ? `-leg${res.__leg.index}` : ''
+                              const key = inBottom ? `transport-after-${res.id}${ls}-${day.id}` : `transport-${res.id}${ls}-${day.id}`
                               if (dropTargetRef.current !== key) setDropTargetKey(key)
                             }}
-                            draggable={canEditDays && spanPhase !== 'middle'}
+                            draggable={canEditDays && spanPhase !== 'middle' && !res.__leg}
                             onDragStart={e => {
-                              if (!canEditDays || spanPhase === 'middle') { e.preventDefault(); return }
+                              if (!canEditDays || spanPhase === 'middle' || res.__leg) { e.preventDefault(); return }
                               // setData is required for the drag to start reliably (Firefox) and
                               // matches how place/note items initiate their drag.
                               e.dataTransfer.setData('reservationId', String(res.id))
@@ -1773,15 +1852,15 @@ const DayPlanSidebar = React.memo(function DayPlanSidebar(props: DayPlanSidebarP
                                 const r2 = reservations.find(x => x.id === Number(fromReservationId))
                                 if (r2) { const update = computeMultiDayMove(r2, day.id, phase); tripActions.updateReservation(tripId, r2.id, update).catch((err: unknown) => toast.error(err instanceof Error ? err.message : t('common.unknownError'))) }
                               } else if (fromReservationId) {
-                                handleMergedDrop(day.id, 'transport', Number(fromReservationId), 'transport', res.id, insertAfter)
+                                handleMergedDrop(day.id, 'transport', Number(fromReservationId), 'transport', res.id, insertAfter, res.__leg?.index ?? null)
                               } else if (fromAssignmentId && fromDayId !== day.id) {
                                 tripActions.moveAssignment(tripId, Number(fromAssignmentId), fromDayId, day.id).catch((err: unknown) => toast.error(err instanceof Error ? err.message : t('common.unknownError')))
                               } else if (fromAssignmentId) {
-                                handleMergedDrop(day.id, 'place', Number(fromAssignmentId), 'transport', res.id, insertAfter)
+                                handleMergedDrop(day.id, 'place', Number(fromAssignmentId), 'transport', res.id, insertAfter, res.__leg?.index ?? null)
                               } else if (noteId && fromDayId !== day.id) {
                                 tripActions.moveDayNote(tripId, fromDayId, day.id, Number(noteId)).catch((err: unknown) => toast.error(err instanceof Error ? err.message : t('common.unknownError')))
                               } else if (noteId) {
-                                handleMergedDrop(day.id, 'note', Number(noteId), 'transport', res.id, insertAfter)
+                                handleMergedDrop(day.id, 'note', Number(noteId), 'transport', res.id, insertAfter, res.__leg?.index ?? null)
                               }
                               setDraggingId(null); setDropTargetKey(null); dragDataRef.current = null; window.__dragData = null
                             }}
@@ -1801,7 +1880,7 @@ const DayPlanSidebar = React.memo(function DayPlanSidebar(props: DayPlanSidebarP
                               opacity: draggingId === res.id ? 0.4 : spanPhase === 'middle' ? 0.65 : 1,
                             }}
                           >
-                            {canEditDays && spanPhase !== 'middle' && (
+                            {canEditDays && spanPhase !== 'middle' && !res.__leg && (
                               <div className="dp-grip" style={{ flexShrink: 0, color: 'var(--text-faint)', display: 'flex', alignItems: 'center', opacity: 0.3, transition: 'opacity 0.15s', cursor: 'grab' }}>
                                 <GripVertical size={13} strokeWidth={1.8} />
                               </div>
@@ -1846,7 +1925,7 @@ const DayPlanSidebar = React.memo(function DayPlanSidebar(props: DayPlanSidebarP
                                 </div>
                               )}
                             </div>
-                            {onToggleConnection && (res.endpoints || []).length >= 2 && (() => {
+                            {onToggleConnection && (!res.__leg || res.__leg.index === 0) && (res.endpoints || []).length >= 2 && (() => {
                               const active = visibleConnectionIds.includes(res.id)
                               return (
                                 <button
@@ -1870,6 +1949,7 @@ const DayPlanSidebar = React.memo(function DayPlanSidebar(props: DayPlanSidebarP
                               )
                             })()}
                           </div>
+                          {routeLegs[res.id] && <RouteConnector seg={routeLegs[res.id]} profile={routeProfile} />}
                           </React.Fragment>
                         )
                       }
@@ -2021,7 +2101,7 @@ const DayPlanSidebar = React.memo(function DayPlanSidebar(props: DayPlanSidebarP
                   </div>
 
                   {/* Routen-Werkzeuge (ausgewählter Tag, 2+ Orte) */}
-                  {isSelected && getDayAssignments(day.id).length >= 2 && (
+                  {(isSelected || (showRouteToolsWhenExpanded && isExpanded)) && getDayAssignments(day.id).length >= 2 && (
                     <div style={{ padding: '10px 16px 12px', borderTop: '1px solid var(--border-faint)', display: 'flex', flexDirection: 'column', gap: 7 }}>
                       <div style={{ display: 'flex', gap: 6, alignItems: 'stretch' }}>
                         <button
@@ -2037,7 +2117,7 @@ const DayPlanSidebar = React.memo(function DayPlanSidebar(props: DayPlanSidebarP
                           <RouteIcon size={12} strokeWidth={2} />
                           {t('dayplan.route')}
                         </button>
-                        <button onClick={handleOptimize} className="bg-surface-hover text-content-secondary" style={{
+                        <button onClick={() => handleOptimize(day.id)} className="bg-surface-hover text-content-secondary" style={{
                           flex: 1, display: 'flex', alignItems: 'center', justifyContent: 'center', gap: 5,
                           padding: '6px 0', fontSize: 11, fontWeight: 500, borderRadius: 8, border: 'none',
                           cursor: 'pointer', fontFamily: 'inherit',
@@ -2066,7 +2146,7 @@ const DayPlanSidebar = React.memo(function DayPlanSidebar(props: DayPlanSidebarP
                           })}
                         </div>
                       </div>
-                      {routeInfo && (
+                      {isSelected && routeInfo && (
                         <div className="text-content-secondary bg-surface-hover" style={{ display: 'flex', justifyContent: 'center', gap: 12, fontSize: 12, borderRadius: 8, padding: '5px 10px' }}>
                           <span>{routeInfo.distance}</span>
                           <span className="text-content-faint">·</span>

client/src/components/Planner/DayPlanSidebarNoteModal.tsx

@@ -58,7 +58,7 @@ export function DayPlanSidebarNoteModal({ noteUi, setNoteUi, noteInputRef, cance
             />
             <textarea
               value={ui.time}
-              maxLength={150}
+              maxLength={250}
               rows={3}
               onChange={e => setNoteUi(prev => ({ ...prev, [dayId]: { ...prev[dayId], time: e.target.value } }))}
               onKeyDown={e => { if (e.key === 'Escape') cancelNote(Number(dayId)) }}
@@ -66,7 +66,7 @@ export function DayPlanSidebarNoteModal({ noteUi, setNoteUi, noteInputRef, cance
               className="text-content"
               style={{ fontSize: 12, border: '1px solid var(--border-primary)', borderRadius: 8, padding: '7px 10px', fontFamily: 'inherit', outline: 'none', width: '100%', boxSizing: 'border-box', resize: 'none', lineHeight: 1.4 }}
             />
-            <div className={(ui.time?.length || 0) >= 140 ? 'text-[#d97706]' : 'text-content-faint'} style={{ textAlign: 'right', fontSize: 11, marginTop: -2 }}>{ui.time?.length || 0}/150</div>
+            <div className={(ui.time?.length || 0) >= 240 ? 'text-[#d97706]' : 'text-content-faint'} style={{ textAlign: 'right', fontSize: 11, marginTop: -2 }}>{ui.time?.length || 0}/250</div>
             <div style={{ display: 'flex', gap: 8, justifyContent: 'flex-end' }}>
               <button onClick={() => cancelNote(Number(dayId))} className="text-content-muted" style={{ fontSize: 12, background: 'none', border: '1px solid var(--border-primary)', borderRadius: 8, padding: '6px 14px', cursor: 'pointer', fontFamily: 'inherit' }}>{t('common.cancel')}</button>
               <button onClick={() => saveNote(Number(dayId))} disabled={!ui.text?.trim()} className={!ui.text?.trim() ? 'bg-[var(--border-primary)] text-content-faint' : 'bg-accent text-accent-text'} style={{ fontSize: 12, border: 'none', borderRadius: 8, padding: '6px 16px', cursor: !ui.text?.trim() ? 'not-allowed' : 'pointer', fontWeight: 600, fontFamily: 'inherit', transition: 'background 0.15s, color 0.15s' }}>

client/src/components/Planner/DayPlanSidebarToolbar.tsx

@@ -1,5 +1,7 @@
-import { ChevronsDownUp, ChevronsUpDown, FileDown, Undo2 } from 'lucide-react'
+import { useState } from 'react'
+import { ChevronsDownUp, ChevronsUpDown, FileDown, Undo2, ArrowUpDown } from 'lucide-react'
 import { downloadTripPDF } from '../PDF/TripPDF'
+import { DayReorderPopup } from './DayReorderPopup'
 import Tooltip from '../shared/Tooltip'
 import { useToast } from '../shared/Toast'
 import type { Trip, Day, Place, Category, AssignmentsMap, Reservation, DayNote } from '../../types'
@@ -27,13 +29,18 @@ interface DayPlanSidebarToolbarProps {
   undoHover: boolean
   setUndoHover: (v: boolean) => void
   lastActionLabel: string | null
+  canEditDays?: boolean
+  onReorderDays?: (orderedIds: number[]) => void
+  onAddDay?: (position?: number) => void
 }
 
 export function DayPlanSidebarToolbar({
   tripId, trip, days, places, categories, assignments, reservations, dayNotes,
   t, locale, toast, pdfHover, setPdfHover, icsHover, setIcsHover,
   expandedDays, setExpandedDays, onUndo, canUndo, undoHover, setUndoHover, lastActionLabel,
+  canEditDays, onReorderDays, onAddDay,
 }: DayPlanSidebarToolbarProps) {
+  const [reorderOpen, setReorderOpen] = useState(false)
   return (
     <div className="border-b border-edge-faint" style={{ padding: '12px 16px', flexShrink: 0 }}>
       <div style={{ display: 'flex', alignItems: 'center', justifyContent: 'flex-end', gap: 8 }}>
@@ -197,6 +204,38 @@ export function DayPlanSidebarToolbar({
             )}
           </div>
         )}
+        {canEditDays && onReorderDays && onAddDay && days.length > 0 && (
+          <div style={{ position: 'relative', flexShrink: 0 }}>
+            <Tooltip label={t('dayplan.reorderDays')} placement="bottom">
+              <button
+                onClick={() => setReorderOpen(v => !v)}
+                aria-label={t('dayplan.reorderDays')}
+                aria-pressed={reorderOpen}
+                style={{
+                  display: 'flex', alignItems: 'center', justifyContent: 'center',
+                  width: 30, height: 30, borderRadius: 8,
+                  border: '1px solid var(--border-primary)',
+                  background: reorderOpen ? 'var(--bg-hover)' : 'none',
+                  color: 'var(--text-primary)', cursor: 'pointer', fontFamily: 'inherit', padding: 0,
+                  transition: 'color 0.15s, border-color 0.15s, background 0.15s',
+                }}
+                onMouseEnter={e => { if (!reorderOpen) e.currentTarget.style.background = 'var(--bg-hover)' }}
+                onMouseLeave={e => { if (!reorderOpen) e.currentTarget.style.background = 'transparent' }}
+              >
+                <ArrowUpDown size={14} strokeWidth={2} />
+              </button>
+            </Tooltip>
+            <DayReorderPopup
+              isOpen={reorderOpen}
+              days={days}
+              t={t}
+              locale={locale}
+              onReorder={onReorderDays}
+              onAddDay={() => onAddDay()}
+              onClose={() => setReorderOpen(false)}
+            />
+          </div>
+        )}
       </div>
     </div>
   )

client/src/components/Planner/DayReorderPopup.tsx

@@ -0,0 +1,143 @@
+import { useState } from 'react'
+import { GripVertical, ArrowUp, ArrowDown, Plus } from 'lucide-react'
+import Modal from '../shared/Modal'
+import type { Day } from '../../types'
+
+interface DayReorderPopupProps {
+  isOpen: boolean
+  days: Day[]
+  t: (key: string, params?: Record<string, any>) => string
+  locale: string
+  onReorder: (orderedIds: number[]) => void
+  onAddDay: () => void
+  onClose: () => void
+}
+
+/**
+ * Modal for moving whole days around: drag a row by its grip or use the up/down
+ * arrows, and add a day at the end. Day headers stay untouched — this is the
+ * single surface for ordering. Reorders are applied optimistically by the store,
+ * so the list reflects each move immediately.
+ */
+export function DayReorderPopup({ isOpen, days, t, locale, onReorder, onAddDay, onClose }: DayReorderPopupProps) {
+  const [dragIndex, setDragIndex] = useState<number | null>(null)
+  const [overIndex, setOverIndex] = useState<number | null>(null)
+
+  const ordered = [...days].sort((a, b) => (a.day_number ?? 0) - (b.day_number ?? 0))
+
+  const label = (day: Day, index: number) => {
+    if (day.title) return day.title
+    if (day.date) {
+      const d = new Date(day.date + 'T00:00:00')
+      return d.toLocaleDateString(locale, { weekday: 'short', day: 'numeric', month: 'short' })
+    }
+    return t('dayplan.dayN', { n: index + 1 })
+  }
+
+  const move = (from: number, to: number) => {
+    if (to < 0 || to >= ordered.length || from === to) return
+    const ids = ordered.map(d => d.id)
+    const [moved] = ids.splice(from, 1)
+    ids.splice(to, 0, moved)
+    onReorder(ids)
+  }
+
+  const cellBtn = {
+    display: 'grid', placeItems: 'center', width: 28, height: 28,
+    border: '1px solid var(--border-faint)', borderRadius: 7,
+    background: 'none', cursor: 'pointer', color: 'var(--text-muted)', padding: 0,
+  } as const
+
+  return (
+    <Modal
+      isOpen={isOpen}
+      onClose={onClose}
+      title={t('dayplan.reorderTitle')}
+      size="md"
+      footer={
+        <div style={{ display: 'flex', alignItems: 'center', justifyContent: 'space-between', gap: 12 }}>
+          <button
+            onClick={onClose}
+            style={{
+              padding: '8px 16px', borderRadius: 8, fontSize: 13, fontWeight: 500,
+              border: '1px solid var(--border-primary)', background: 'none',
+              color: 'var(--text-muted)', cursor: 'pointer', fontFamily: 'inherit',
+            }}
+          >
+            {t('common.close')}
+          </button>
+          <button
+            onClick={onAddDay}
+            className="bg-accent text-accent-text"
+            style={{
+              display: 'flex', alignItems: 'center', gap: 6, padding: '8px 16px',
+              borderRadius: 8, border: 'none', fontSize: 13, fontWeight: 500,
+              cursor: 'pointer', fontFamily: 'inherit',
+            }}
+          >
+            <Plus size={15} strokeWidth={2} />
+            {t('dayplan.addDay')}
+          </button>
+        </div>
+      }
+    >
+      <p style={{ margin: '0 0 14px', fontSize: 12.5, color: 'var(--text-faint)', lineHeight: 1.4 }}>
+        {t('dayplan.reorderHint')}
+      </p>
+
+      <div style={{ display: 'flex', flexDirection: 'column', gap: 4 }}>
+        {ordered.map((day, index) => (
+          <div
+            key={day.id}
+            draggable
+            onDragStart={() => setDragIndex(index)}
+            onDragEnd={() => { setDragIndex(null); setOverIndex(null) }}
+            onDragOver={e => { e.preventDefault(); if (overIndex !== index) setOverIndex(index) }}
+            onDrop={e => {
+              e.preventDefault()
+              if (dragIndex !== null && dragIndex !== index) move(dragIndex, index)
+              setDragIndex(null); setOverIndex(null)
+            }}
+            style={{
+              display: 'flex', alignItems: 'center', gap: 10, padding: '8px 10px',
+              borderRadius: 9,
+              border: '1px solid var(--border-faint)',
+              background: overIndex === index && dragIndex !== null && dragIndex !== index ? 'var(--bg-hover)' : 'var(--bg-card, white)',
+              opacity: dragIndex === index ? 0.5 : 1,
+              outline: overIndex === index && dragIndex !== null && dragIndex !== index ? '2px dashed var(--border-primary)' : 'none',
+              outlineOffset: -2,
+            }}
+          >
+            <GripVertical size={15} strokeWidth={1.8} style={{ cursor: 'grab', color: 'var(--text-faint)', flexShrink: 0 }} />
+            <span style={{
+              flexShrink: 0, width: 24, height: 24, borderRadius: '50%',
+              background: 'var(--bg-hover)', color: 'var(--text-muted)',
+              display: 'grid', placeItems: 'center', fontSize: 11, fontWeight: 700,
+            }}>
+              {index + 1}
+            </span>
+            <span style={{ flex: 1, minWidth: 0, fontSize: 13.5, fontWeight: 500, overflow: 'hidden', textOverflow: 'ellipsis', whiteSpace: 'nowrap' }}>
+              {label(day, index)}
+            </span>
+            <button
+              onClick={() => move(index, index - 1)}
+              disabled={index === 0}
+              aria-label={t('dayplan.moveUp')}
+              style={{ ...cellBtn, opacity: index === 0 ? 0.35 : 1, cursor: index === 0 ? 'default' : 'pointer' }}
+            >
+              <ArrowUp size={14} strokeWidth={2} />
+            </button>
+            <button
+              onClick={() => move(index, index + 1)}
+              disabled={index === ordered.length - 1}
+              aria-label={t('dayplan.moveDown')}
+              style={{ ...cellBtn, opacity: index === ordered.length - 1 ? 0.35 : 1, cursor: index === ordered.length - 1 ? 'default' : 'pointer' }}
+            >
+              <ArrowDown size={14} strokeWidth={2} />
+            </button>
+          </div>
+        ))}
+      </div>
+    </Modal>
+  )
+}

client/src/components/Planner/PlaceFormModal.tsx

@@ -27,7 +27,7 @@ interface PlaceFormModalProps {
   onClose: () => void
   onSave: (data: PlaceSubmitData, files?: File[]) => Promise<void> | void
   place: Place | null
-  prefillCoords?: { lat: number; lng: number; name?: string; address?: string } | null
+  prefillCoords?: { lat: number; lng: number; name?: string; address?: string; website?: string; phone?: string; osm_id?: string } | null
   tripId: number
   categories: Category[]
   onCategoryCreated: (category: { name: string; color?: string; icon?: string }) => Promise<Category> | undefined
@@ -39,6 +39,31 @@ interface PlaceFormModalProps {
 /** Place create/edit form state: maps search + Google-URL resolve + autocomplete,
  * category creation, file attachments and submit. Keeps PlaceFormModal a thin
  * render over the form fields. */
+
+// #1152: a manually-added place is treated as a likely duplicate of an existing
+// trip place if it shares the Google Place ID, the (case-insensitive) name, or
+// near-identical coordinates (~11 m). Mirrors the server-side import dedup.
+const DUP_COORD_TOLERANCE = 0.0001
+function findDuplicatePlace(
+  form: PlaceFormData,
+  places: { name?: string | null; lat?: number | null; lng?: number | null; google_place_id?: string | null }[],
+): { name?: string | null } | null {
+  const name = (form.name || '').trim().toLowerCase()
+  const gid = (form.google_place_id || '').trim()
+  const lat = form.lat ? parseFloat(form.lat) : null
+  const lng = form.lng ? parseFloat(form.lng) : null
+  for (const p of places || []) {
+    if (gid && p.google_place_id && p.google_place_id === gid) return p
+    if (name && p.name && p.name.trim().toLowerCase() === name) return p
+    if (
+      lat != null && lng != null && p.lat != null && p.lng != null &&
+      Math.abs(Number(p.lat) - lat) <= DUP_COORD_TOLERANCE &&
+      Math.abs(Number(p.lng) - lng) <= DUP_COORD_TOLERANCE
+    ) return p
+  }
+  return null
+}
+
 function usePlaceFormModal(props: PlaceFormModalProps) {
   const {
   isOpen, onClose, onSave, place, prefillCoords, tripId, categories,
@@ -51,6 +76,7 @@ function usePlaceFormModal(props: PlaceFormModalProps) {
   const [newCategoryName, setNewCategoryName] = useState('')
   const [showNewCategory, setShowNewCategory] = useState(false)
   const [isSaving, setIsSaving] = useState(false)
+  const [duplicateWarning, setDuplicateWarning] = useState<string | null>(null)
   const [pendingFiles, setPendingFiles] = useState([])
   const fileRef = useRef(null)
   const [acSuggestions, setAcSuggestions] = useState<{ placeId: string; mainText: string; secondaryText: string }[]>([])
@@ -86,11 +112,15 @@ function usePlaceFormModal(props: PlaceFormModalProps) {
         lng: String(prefillCoords.lng),
         name: prefillCoords.name || '',
         address: prefillCoords.address || '',
+        website: prefillCoords.website || '',
+        phone: prefillCoords.phone || '',
+        osm_id: prefillCoords.osm_id,
       })
     } else {
       setForm(DEFAULT_FORM)
     }
     setPendingFiles([])
+    setDuplicateWarning(null)
   }, [place, prefillCoords, isOpen])
 
   // Derive location bias bounding box from the trip's existing places
@@ -306,6 +336,17 @@ function usePlaceFormModal(props: PlaceFormModalProps) {
       toast.error(t('places.nameRequired'))
       return
     }
+    // #1152: only for new places, and only on the first attempt — a second click
+    // (with the warning already showing) is the explicit "add anyway" confirmation.
+    if (!place && !duplicateWarning) {
+      const dup = findDuplicatePlace(form, places)
+      if (dup) {
+        const dupName = dup.name || form.name
+        setDuplicateWarning(dupName)
+        toast.warning(t('places.duplicateExists', { name: dupName }))
+        return
+      }
+    }
     setIsSaving(true)
     try {
       await onSave({
@@ -378,6 +419,7 @@ function usePlaceFormModal(props: PlaceFormModalProps) {
     handlePaste,
     hasTimeError,
     handleSubmit,
+    duplicateWarning,
   }
 }
 
@@ -438,6 +480,7 @@ export default function PlaceFormModal(props: PlaceFormModalProps) {
     handlePaste,
     hasTimeError,
     handleSubmit,
+    duplicateWarning,
   } = S
   return (
     <Modal
@@ -460,7 +503,7 @@ export default function PlaceFormModal(props: PlaceFormModalProps) {
             disabled={isSaving || hasTimeError}
             className="px-6 py-2 bg-slate-900 text-white text-sm rounded-lg hover:bg-slate-700 disabled:opacity-60 font-medium"
           >
-            {isSaving ? t('common.saving') : place ? t('common.update') : t('common.add')}
+            {isSaving ? t('common.saving') : place ? t('common.update') : duplicateWarning ? t('places.addAnyway') : t('common.add')}
           </button>
         </div>
       }

client/src/components/Planner/PlacesSidebarListImportModal.tsx

@@ -1,10 +1,12 @@
 import ReactDOM from 'react-dom'
+import ToggleSwitch from '../Settings/ToggleSwitch'
 import type { SidebarState } from './usePlacesSidebar'
 
 export function ListImportModal(S: SidebarState) {
   const {
     setListImportOpen, setListImportUrl, t, hasMultipleListImportProviders, availableListImportProviders,
     listImportProvider, setListImportProvider, listImportUrl, listImportLoading, handleListImport,
+    listImportEnrich, setListImportEnrich, canEnrichImport,
   } = S
   return ReactDOM.createPortal(
     <div
@@ -55,6 +57,15 @@ export function ListImportModal(S: SidebarState) {
             fontFamily: 'inherit', boxSizing: 'border-box',
           }}
         />
+        {canEnrichImport && (
+          <div style={{ display: 'flex', alignItems: 'flex-start', gap: 12, marginTop: 12 }}>
+            <div style={{ flex: 1, minWidth: 0 }}>
+              <div className="text-content" style={{ fontSize: 12, fontWeight: 600 }}>{t('places.enrichOnImport')}</div>
+              <div className="text-content-faint" style={{ fontSize: 12, marginTop: 2 }}>{t('places.enrichOnImportHint')}</div>
+            </div>
+            <ToggleSwitch on={listImportEnrich} onToggle={() => setListImportEnrich(!listImportEnrich)} />
+          </div>
+        )}
         <div style={{ display: 'flex', gap: 8, marginTop: 16, justifyContent: 'flex-end' }}>
           <button
             onClick={() => { setListImportOpen(false); setListImportUrl('') }}

client/src/components/Planner/ReservationsPanel.tsx

@@ -179,6 +179,16 @@ function ReservationCard({ r, tripId, onEdit, onDelete, files = [], onNavigateTo
               {t('reservations.needsReview')}
             </span>
           ) : null}
+          {r.external_source === 'airtrail' ? (
+            <span
+              className={r.sync_enabled ? 'text-[#2563eb] bg-[rgba(59,130,246,0.12)]' : 'text-content-faint bg-surface-tertiary'}
+              style={{ display: 'inline-flex', alignItems: 'center', gap: 4, fontSize: 11, fontWeight: 600, padding: '3px 8px', borderRadius: 6 }}
+              title={r.sync_enabled ? t('reservations.airtrail.syncedHint') : t('reservations.airtrail.notSyncedHint')}
+            >
+              <Plane size={11} />
+              {r.sync_enabled ? t('reservations.airtrail.synced') : t('reservations.airtrail.notSynced')}
+            </span>
+          ) : null}
         </div>
         <div style={{ display: 'flex', alignItems: 'center', gap: 2 }}>
           <span className="text-content" style={{
@@ -271,19 +281,21 @@ function ReservationCard({ r, tripId, onEdit, onDelete, files = [], onNavigateTo
         )}
 
         {(() => {
-          const eps = r.endpoints || []
-          const from = eps.find(e => e.role === 'from')
-          const to = eps.find(e => e.role === 'to')
-          if (!from || !to) return null
+          // Full route over all waypoints (from · stops · to), ordered by sequence.
+          const eps = (r.endpoints || []).slice().sort((a, b) => (a.sequence ?? 0) - (b.sequence ?? 0))
+          if (eps.length < 2) return null
           return (
             <div className="bg-surface-tertiary text-content" style={{
               display: 'flex', alignItems: 'center', justifyContent: 'center', gap: 8,
               padding: '8px 12px', borderRadius: 10,
-              fontSize: 12.5,
+              fontSize: 12.5, flexWrap: 'wrap',
             }}>
-              <span style={{ fontWeight: 500, whiteSpace: 'nowrap', overflow: 'hidden', textOverflow: 'ellipsis' }}>{from.name}</span>
-              <TypeIcon size={14} style={{ color: typeInfo.color, flexShrink: 0 }} />
-              <span style={{ fontWeight: 500, whiteSpace: 'nowrap', overflow: 'hidden', textOverflow: 'ellipsis' }}>{to.name}</span>
+              {eps.map((ep, i) => (
+                <span key={i} style={{ display: 'inline-flex', alignItems: 'center', gap: 8, minWidth: 0 }}>
+                  {i > 0 && <TypeIcon size={14} style={{ color: typeInfo.color, flexShrink: 0 }} />}
+                  <span style={{ fontWeight: 500, whiteSpace: 'nowrap', overflow: 'hidden', textOverflow: 'ellipsis' }}>{ep.name}</span>
+                </span>
+              ))}
             </div>
           )
         })()}
@@ -470,6 +482,8 @@ interface ReservationsPanelProps {
   onAdd: () => void
   onImport?: () => void
   bookingImportAvailable?: boolean
+  onAirTrailImport?: () => void
+  airTrailAvailable?: boolean
   onEdit: (reservation: Reservation) => void
   onDelete: (id: number) => void
   onNavigateToFiles: () => void
@@ -477,7 +491,7 @@ interface ReservationsPanelProps {
   addManualKey?: string
 }
 
-export default function ReservationsPanel({ tripId, reservations, days, assignments, files = [], onAdd, onImport, bookingImportAvailable, onEdit, onDelete, onNavigateToFiles, titleKey = 'reservations.title', addManualKey = 'reservations.addManual' }: ReservationsPanelProps) {
+export default function ReservationsPanel({ tripId, reservations, days, assignments, files = [], onAdd, onImport, bookingImportAvailable, onAirTrailImport, airTrailAvailable, onEdit, onDelete, onNavigateToFiles, titleKey = 'reservations.title', addManualKey = 'reservations.addManual' }: ReservationsPanelProps) {
   const { t, locale } = useTranslation()
   const can = useCanDo()
   const trip = useTripStore((s) => s.trip)
@@ -600,6 +614,21 @@ export default function ReservationsPanel({ tripId, reservations, days, assignme
                   <span className="hidden sm:inline">{t('reservations.import.cta')}</span>
                 </button>
               )}
+              {onAirTrailImport && airTrailAvailable && (
+                <button onClick={onAirTrailImport} className="bg-surface-secondary text-content" style={{
+                  appearance: 'none', border: '1px solid var(--border-primary)', cursor: 'pointer', fontFamily: 'inherit',
+                  display: 'inline-flex', alignItems: 'center', gap: 6,
+                  padding: '8px 14px', borderRadius: 10, fontSize: 13, fontWeight: 500, boxSizing: 'border-box',
+                  transition: 'opacity 0.15s ease',
+                }}
+                  onMouseEnter={e => e.currentTarget.style.opacity = '0.75'}
+                  onMouseLeave={e => e.currentTarget.style.opacity = '1'}
+                  title={t('reservations.airtrail.title')}
+                >
+                  <Plane size={14} strokeWidth={2} />
+                  <span className="hidden sm:inline">{t('reservations.airtrail.cta')}</span>
+                </button>
+              )}
               <button onClick={onAdd} className="bg-accent text-accent-text" style={{
                 appearance: 'none', border: 'none', cursor: 'pointer', fontFamily: 'inherit',
                 display: 'inline-flex', alignItems: 'center', gap: 6,

client/src/components/Planner/TransportModal.tsx

@@ -1,6 +1,6 @@
 import { useState, useEffect, useMemo, useRef } from 'react'
 import { useParams } from 'react-router-dom'
-import { Plane, Train, Car, Ship, Bus, Sailboat, Bike, CarTaxiFront, Route, Paperclip, FileText, X, ExternalLink, Link2 } from 'lucide-react'
+import { Plane, Train, Car, Ship, Bus, Sailboat, Bike, CarTaxiFront, Route, Paperclip, FileText, X, ExternalLink, Link2, Plus, Trash2 } from 'lucide-react'
 import Modal from '../shared/Modal'
 import CustomSelect from '../shared/CustomSelect'
 import CustomTimePicker from '../shared/CustomTimePicker'
@@ -14,6 +14,7 @@ import { formatDate, splitReservationDateTime } from '../../utils/formatters'
 import { openFile } from '../../utils/fileDownload'
 import apiClient from '../../api/client'
 import type { Day, Reservation, ReservationEndpoint, TripFile } from '../../types'
+import { parseReservationMetadata, orderedEndpoints } from '../../utils/flightLegs'
 
 const TRANSPORT_TYPES = ['flight', 'train', 'bus', 'car', 'taxi', 'bicycle', 'cruise', 'ferry', 'transport_other'] as const
 type TransportType = typeof TRANSPORT_TYPES[number]
@@ -23,7 +24,7 @@ interface EndpointPick {
   location?: LocationPoint
 }
 
-function endpointFromAirport(a: Airport, role: 'from' | 'to', sequence: number, date: string | null, time: string | null): Omit<ReservationEndpoint, 'id' | 'reservation_id'> {
+function endpointFromAirport(a: Airport, role: 'from' | 'to' | 'stop', sequence: number, date: string | null, time: string | null): Omit<ReservationEndpoint, 'id' | 'reservation_id'> {
   return {
     role, sequence,
     name: a.city ? `${a.city} (${a.iata})` : a.name,
@@ -63,6 +64,25 @@ function locationFromEndpoint(e: ReservationEndpoint | undefined): LocationPoint
   return { name: e.name, lat: e.lat, lng: e.lng, address: null }
 }
 
+// ── Multi-leg flight waypoints ─────────────────────────────────────────────
+// A flight is an ordered list of airports. The origin has only a departure, the
+// destination only an arrival, and each intermediate stop has both — plus the
+// airline/flight number of the flight LEAVING it. N waypoints = N-1 legs. A
+// single-leg flight is just two waypoints, so it persists exactly as before.
+interface WaypointForm {
+  airport: Airport | null
+  arrDayId: string | number
+  arrTime: string
+  depDayId: string | number
+  depTime: string
+  airline: string
+  flight_number: string
+  seat: string
+}
+function emptyWaypoint(dayId: string | number = ''): WaypointForm {
+  return { airport: null, arrDayId: dayId, arrTime: '', depDayId: dayId, depTime: '', airline: '', flight_number: '', seat: '' }
+}
+
 const TYPE_OPTIONS = [
   { value: 'flight',          labelKey: 'reservations.type.flight',          Icon: Plane },
   { value: 'train',           labelKey: 'reservations.type.train',           Icon: Train },
@@ -122,6 +142,8 @@ export function TransportModal({ isOpen, onClose, onSave, reservation, days, sel
   const [isSaving, setIsSaving] = useState(false)
   const [fromPick, setFromPick] = useState<EndpointPick>({})
   const [toPick, setToPick] = useState<EndpointPick>({})
+  // Flight route as an ordered list of airports (origin .. stops .. destination).
+  const [waypoints, setWaypoints] = useState<WaypointForm[]>([emptyWaypoint(), emptyWaypoint()])
   const [uploadingFile, setUploadingFile] = useState(false)
   const [pendingFiles, setPendingFiles] = useState<File[]>([])
   const [showFilePicker, setShowFilePicker] = useState(false)
@@ -159,8 +181,40 @@ export function TransportModal({ isOpen, onClose, onSave, reservation, days, sel
         budget_category: (meta.budget_category && budgetItems.some(i => i.category === meta.budget_category)) ? meta.budget_category : '',
       })
       if (type === 'flight') {
-        setFromPick({ airport: airportFromEndpoint(from) || undefined })
-        setToPick({ airport: airportFromEndpoint(to) || undefined })
+        const orderedEps = orderedEndpoints(reservation)
+        const metaLegs: any[] = Array.isArray(meta.legs) ? meta.legs : []
+        let wps: WaypointForm[]
+        if (orderedEps.length >= 2) {
+          wps = orderedEps.map((ep, i) => {
+            const legInto = metaLegs[i - 1] // leg arriving INTO waypoint i
+            const legOut = metaLegs[i] // leg departing FROM waypoint i
+            const isFirst = i === 0
+            const isLast = i === orderedEps.length - 1
+            return {
+              airport: airportFromEndpoint(ep),
+              arrDayId: legInto?.arr_day_id ?? (isLast ? (reservation.end_day_id ?? '') : ''),
+              arrTime: legInto?.arr_time ?? (!isFirst ? (ep.local_time ?? '') : ''),
+              depDayId: legOut?.dep_day_id ?? (isFirst ? (reservation.day_id ?? '') : ''),
+              depTime: legOut?.dep_time ?? (!isLast ? (ep.local_time ?? '') : ''),
+              airline: legOut?.airline ?? (isFirst ? (meta.airline ?? '') : ''),
+              flight_number: legOut?.flight_number ?? (isFirst ? (meta.flight_number ?? '') : ''),
+              seat: legOut?.seat ?? (isFirst ? (meta.seat ?? '') : ''),
+            }
+          })
+        } else {
+          // Legacy flight with no (or partial) endpoints — seed two waypoints.
+          const dep = emptyWaypoint(reservation.day_id ?? '')
+          dep.airport = airportFromEndpoint(from)
+          dep.depTime = splitReservationDateTime(reservation.reservation_time).time ?? ''
+          dep.airline = meta.airline ?? ''
+          dep.flight_number = meta.flight_number ?? ''
+          dep.seat = meta.seat ?? ''
+          const arr = emptyWaypoint(reservation.end_day_id ?? reservation.day_id ?? '')
+          arr.airport = airportFromEndpoint(to)
+          arr.arrTime = splitReservationDateTime(reservation.reservation_end_time).time ?? ''
+          wps = [dep, arr]
+        }
+        setWaypoints(wps)
       } else {
         setFromPick({ location: locationFromEndpoint(from) || undefined })
         setToPick({ location: locationFromEndpoint(to) || undefined })
@@ -169,6 +223,7 @@ export function TransportModal({ isOpen, onClose, onSave, reservation, days, sel
       setForm({ ...defaultForm, start_day_id: selectedDayId ?? '', end_day_id: selectedDayId ?? '' })
       setFromPick({})
       setToPick({})
+      setWaypoints([emptyWaypoint(selectedDayId ?? ''), emptyWaypoint(selectedDayId ?? '')])
     }
   }, [isOpen, reservation, selectedDayId, budgetItems])
 
@@ -187,18 +242,48 @@ export function TransportModal({ isOpen, onClose, onSave, reservation, days, sel
         return day?.date ? `${day.date}T${time}` : time
       }
 
-      const metadata: Record<string, string> = {}
+      const dayDate = (id: string | number): string | null => days.find(d => d.id === Number(id))?.date ?? null
+      // Flight route as an ordered list of airports (origin .. stops .. destination).
+      const flightWps = form.type === 'flight' ? waypoints.filter(w => w.airport) : []
+      const firstWp = flightWps[0]
+      const lastWp = flightWps[flightWps.length - 1]
+      // Per-leg day-plan positions are owned by the day planner, not this form — keep
+      // them when re-saving so editing a flight doesn't reset where its legs sit.
+      const origLegs: any[] = reservation ? (parseReservationMetadata(reservation).legs || []) : []
+
+      const metadata: Record<string, any> = {}
       if (form.type === 'flight') {
-        if (form.meta_airline) metadata.airline = form.meta_airline
-        if (form.meta_flight_number) metadata.flight_number = form.meta_flight_number
-        if (fromPick.airport) {
-          metadata.departure_airport = fromPick.airport.iata
-          metadata.departure_timezone = fromPick.airport.tz
+        // Top-level keys mirror the first/last leg so legacy readers keep working.
+        if (firstWp?.airline) metadata.airline = firstWp.airline
+        if (firstWp?.flight_number) metadata.flight_number = firstWp.flight_number
+        if (firstWp?.airport) {
+          metadata.departure_airport = firstWp.airport.iata
+          metadata.departure_timezone = firstWp.airport.tz
         }
-        if (toPick.airport) {
-          metadata.arrival_airport = toPick.airport.iata
-          metadata.arrival_timezone = toPick.airport.tz
+        if (lastWp?.airport) {
+          metadata.arrival_airport = lastWp.airport.iata
+          metadata.arrival_timezone = lastWp.airport.tz
         }
+        // Per-leg detail only for true multi-leg flights — a single-leg flight
+        // keeps the exact same (flat) metadata it had before this feature.
+        if (flightWps.length > 2) {
+          metadata.legs = flightWps.slice(0, -1).map((w, i) => {
+            const next = flightWps[i + 1]
+            return {
+              from: w.airport!.iata,
+              to: next.airport!.iata,
+              ...(w.airline ? { airline: w.airline } : {}),
+              ...(w.flight_number ? { flight_number: w.flight_number } : {}),
+              ...(w.seat ? { seat: w.seat } : {}),
+              dep_day_id: w.depDayId ? Number(w.depDayId) : null,
+              dep_time: w.depTime || null,
+              arr_day_id: next.arrDayId ? Number(next.arrDayId) : null,
+              arr_time: next.arrTime || null,
+              ...(origLegs[i]?.day_positions ? { day_positions: origLegs[i].day_positions } : {}),
+            }
+          })
+        }
+        if (firstWp?.seat) metadata.seat = firstWp.seat
       } else if (form.type === 'train') {
         if (form.meta_train_number) metadata.train_number = form.meta_train_number
         if (form.meta_platform) metadata.platform = form.meta_platform
@@ -213,21 +298,35 @@ export function TransportModal({ isOpen, onClose, onSave, reservation, days, sel
       const endDate = (endDay ?? startDay)?.date ?? null
       const endpoints: ReturnType<typeof endpointFromAirport>[] = []
       if (form.type === 'flight') {
-        if (fromPick.airport) endpoints.push(endpointFromAirport(fromPick.airport, 'from', 0, startDate, form.departure_time || null))
-        if (toPick.airport) endpoints.push(endpointFromAirport(toPick.airport, 'to', 1, endDate, form.arrival_time || null))
+        flightWps.forEach((w, i) => {
+          const isFirst = i === 0
+          const isLast = i === flightWps.length - 1
+          const role: 'from' | 'to' | 'stop' = isFirst ? 'from' : isLast ? 'to' : 'stop'
+          const dId = isLast ? w.arrDayId : w.depDayId
+          const time = isLast ? w.arrTime : w.depTime
+          endpoints.push(endpointFromAirport(w.airport!, role, i, dayDate(dId), time || null))
+        })
       } else {
         if (fromPick.location) endpoints.push(endpointFromLocation(fromPick.location, 'from', 0, startDate, form.departure_time || null))
         if (toPick.location) endpoints.push(endpointFromLocation(toPick.location, 'to', 1, endDate, form.arrival_time || null))
       }
 
+      // Flights derive their span from the first/last waypoint; other transports
+      // keep using the single departure/arrival form fields unchanged.
+      const flightDepDay = firstWp && firstWp.depDayId ? Number(firstWp.depDayId) : null
+      const flightArrDay = lastWp && lastWp.arrDayId ? Number(lastWp.arrDayId) : null
       const payload = {
         title: form.title,
         type: form.type,
         status: form.status,
-        day_id: form.start_day_id ? Number(form.start_day_id) : null,
-        end_day_id: form.end_day_id ? Number(form.end_day_id) : null,
-        reservation_time: buildTime(startDay, form.departure_time),
-        reservation_end_time: buildTime(endDay ?? startDay, form.arrival_time),
+        day_id: form.type === 'flight' ? flightDepDay : (form.start_day_id ? Number(form.start_day_id) : null),
+        end_day_id: form.type === 'flight' ? flightArrDay : (form.end_day_id ? Number(form.end_day_id) : null),
+        reservation_time: form.type === 'flight'
+          ? buildTime(days.find(d => d.id === flightDepDay), firstWp?.depTime || '')
+          : buildTime(startDay, form.departure_time),
+        reservation_end_time: form.type === 'flight'
+          ? buildTime(days.find(d => d.id === flightArrDay), lastWp?.arrTime || '')
+          : buildTime(endDay ?? startDay, form.arrival_time),
         location: null,
         confirmation_number: form.confirmation_number || null,
         notes: form.notes || null,
@@ -348,100 +447,130 @@ export function TransportModal({ isOpen, onClose, onSave, reservation, days, sel
             placeholder={t('reservations.titlePlaceholder')} className={inputClass} />
         </div>
 
-        {/* From / To endpoints */}
-        <div className="grid grid-cols-1 sm:grid-cols-2 gap-3">
-          <div>
-            <label className={labelClass}>{t('reservations.meta.from')}</label>
-            {form.type === 'flight' ? (
-              <AirportSelect value={fromPick.airport || null} onChange={a => setFromPick({ airport: a || undefined })} />
-            ) : (
-              <LocationSelect value={fromPick.location || null} onChange={l => setFromPick({ location: l || undefined })} />
-            )}
+        {form.type === 'flight' ? (
+          /* ── Flight route: ordered airports (origin · stops · destination) ── */
+          <div style={{ display: 'flex', flexDirection: 'column', gap: 8 }}>
+            <label className={labelClass}>{t('reservations.layover.route')}</label>
+            {waypoints.map((wp, i) => {
+              const isFirst = i === 0
+              const isLast = i === waypoints.length - 1
+              const updateWp = (patch: Partial<WaypointForm>) => setWaypoints(prev => prev.map((w, j) => (j === i ? { ...w, ...patch } : w)))
+              const roleLabel = isFirst ? t('reservations.meta.from') : isLast ? t('reservations.meta.to') : t('reservations.layover.stop')
+              return (
+                <div key={i} style={{ display: 'flex', flexDirection: 'column', gap: 6 }}>
+                  <div className="bg-surface-card" style={{ border: '1px solid var(--border-primary)', borderRadius: 10, padding: 10, display: 'flex', flexDirection: 'column', gap: 8 }}>
+                    <div style={{ display: 'flex', alignItems: 'center', gap: 8 }}>
+                      <span className="text-content-faint" style={{ fontSize: 10, fontWeight: 700, textTransform: 'uppercase', letterSpacing: '0.03em', flexShrink: 0 }}>{roleLabel}</span>
+                      <div style={{ flex: 1, minWidth: 0 }}>
+                        <AirportSelect value={wp.airport} onChange={a => updateWp({ airport: a || null })} />
+                      </div>
+                      {!isFirst && !isLast && (
+                        <button type="button" onClick={() => setWaypoints(prev => prev.filter((_, j) => j !== i))} aria-label={t('common.delete')} className="text-content-faint" style={{ background: 'none', border: 'none', cursor: 'pointer', display: 'flex', padding: 4, flexShrink: 0 }}>
+                          <Trash2 size={14} />
+                        </button>
+                      )}
+                    </div>
+                    {!isFirst && (
+                      <div style={{ display: 'flex', gap: 8 }}>
+                        <div style={{ flex: 1, minWidth: 0 }}>
+                          <label className={labelClass}>{t('reservations.arrivalDate')}</label>
+                          <CustomSelect value={wp.arrDayId} onChange={v => updateWp({ arrDayId: v })} placeholder={t('dayplan.dayN', { n: '?' })} options={dayOptions} size="sm" />
+                        </div>
+                        <div style={{ flex: 1, minWidth: 0 }}>
+                          <label className={labelClass}>{t('reservations.arrivalTime')}</label>
+                          <CustomTimePicker value={wp.arrTime} onChange={v => updateWp({ arrTime: v })} />
+                        </div>
+                        {wp.airport && (
+                          <div style={{ flex: 1, minWidth: 0 }}>
+                            <label className={labelClass}>{t('reservations.meta.arrivalTimezone')}</label>
+                            <div className={inputClass} style={{ padding: '8px 12px', color: 'var(--text-muted)', fontSize: 12, background: 'var(--bg-tertiary)' }}>{wp.airport.tz}</div>
+                          </div>
+                        )}
+                      </div>
+                    )}
+                    {!isLast && (
+                      <>
+                        <div style={{ display: 'flex', gap: 8 }}>
+                          <div style={{ flex: 1, minWidth: 0 }}>
+                            <label className={labelClass}>{t('reservations.departureDate')}</label>
+                            <CustomSelect value={wp.depDayId} onChange={v => updateWp({ depDayId: v })} placeholder={t('dayplan.dayN', { n: '?' })} options={dayOptions} size="sm" />
+                          </div>
+                          <div style={{ flex: 1, minWidth: 0 }}>
+                            <label className={labelClass}>{t('reservations.departureTime')}</label>
+                            <CustomTimePicker value={wp.depTime} onChange={v => updateWp({ depTime: v })} />
+                          </div>
+                          {wp.airport && (
+                            <div style={{ flex: 1, minWidth: 0 }}>
+                              <label className={labelClass}>{t('reservations.meta.departureTimezone')}</label>
+                              <div className={inputClass} style={{ padding: '8px 12px', color: 'var(--text-muted)', fontSize: 12, background: 'var(--bg-tertiary)' }}>{wp.airport.tz}</div>
+                            </div>
+                          )}
+                        </div>
+                        <div className="grid grid-cols-1 sm:grid-cols-3 gap-3">
+                          <div>
+                            <label className={labelClass}>{t('reservations.meta.airline')}</label>
+                            <input type="text" value={wp.airline} onChange={e => updateWp({ airline: e.target.value })} placeholder="Lufthansa" className={inputClass} />
+                          </div>
+                          <div>
+                            <label className={labelClass}>{t('reservations.meta.flightNumber')}</label>
+                            <input type="text" value={wp.flight_number} onChange={e => updateWp({ flight_number: e.target.value })} placeholder="LH 123" className={inputClass} />
+                          </div>
+                          <div>
+                            <label className={labelClass}>{t('reservations.meta.seat')}</label>
+                            <input type="text" value={wp.seat} onChange={e => updateWp({ seat: e.target.value })} placeholder="12A" className={inputClass} />
+                          </div>
+                        </div>
+                      </>
+                    )}
+                  </div>
+                  {!isLast && (
+                    <button type="button" onClick={() => setWaypoints(prev => [...prev.slice(0, i + 1), emptyWaypoint(prev[i]?.depDayId || ''), ...prev.slice(i + 1)])}
+                      className="text-content-faint hover:text-content-secondary" style={{ width: '100%', display: 'flex', alignItems: 'center', justifyContent: 'center', gap: 5, padding: '6px 10px', border: '1px dashed var(--border-primary)', borderRadius: 8, background: 'none', fontSize: 11, cursor: 'pointer', fontFamily: 'inherit' }}>
+                      <Plus size={12} /> {t('reservations.layover.addStop')}
+                    </button>
+                  )}
+                </div>
+              )
+            })}
           </div>
-          <div>
-            <label className={labelClass}>{t('reservations.meta.to')}</label>
-            {form.type === 'flight' ? (
-              <AirportSelect value={toPick.airport || null} onChange={a => setToPick({ airport: a || undefined })} />
-            ) : (
-              <LocationSelect value={toPick.location || null} onChange={l => setToPick({ location: l || undefined })} />
-            )}
-          </div>
-        </div>
-
-        {/* Departure row */}
-        <div style={{ display: 'flex', gap: 8 }}>
-          <div style={{ flex: 1, minWidth: 0 }}>
-            <label className={labelClass}>
-              {form.type === 'flight' ? t('reservations.departureDate') : form.type === 'car' ? t('reservations.pickupDate') : t('reservations.date')}
-            </label>
-            <CustomSelect
-              value={form.start_day_id}
-              onChange={value => set('start_day_id', value)}
-              placeholder={t('dayplan.dayN', { n: '?' })}
-              options={dayOptions}
-              size="sm"
-            />
-          </div>
-          <div style={{ flex: 1, minWidth: 0 }}>
-            <label className={labelClass}>
-              {form.type === 'flight' ? t('reservations.departureTime') : form.type === 'car' ? t('reservations.pickupTime') : t('reservations.startTime')}
-            </label>
-            <CustomTimePicker value={form.departure_time} onChange={v => set('departure_time', v)} />
-          </div>
-          {form.type === 'flight' && fromPick.airport && (
-            <div style={{ flex: 1, minWidth: 0 }}>
-              <label className={labelClass}>{t('reservations.meta.departureTimezone')}</label>
-              <div className={inputClass} style={{ padding: '8px 12px', color: 'var(--text-muted)', fontSize: 12, background: 'var(--bg-tertiary)' }}>
-                {fromPick.airport.tz}
+        ) : (
+          <>
+            {/* From / To endpoints (non-flight) */}
+            <div className="grid grid-cols-1 sm:grid-cols-2 gap-3">
+              <div>
+                <label className={labelClass}>{t('reservations.meta.from')}</label>
+                <LocationSelect value={fromPick.location || null} onChange={l => setFromPick({ location: l || undefined })} />
+              </div>
+              <div>
+                <label className={labelClass}>{t('reservations.meta.to')}</label>
+                <LocationSelect value={toPick.location || null} onChange={l => setToPick({ location: l || undefined })} />
               </div>
             </div>
-          )}
-        </div>
 
-        {/* Arrival row */}
-        <div style={{ display: 'flex', gap: 8 }}>
-          <div style={{ flex: 1, minWidth: 0 }}>
-            <label className={labelClass}>
-              {form.type === 'flight' ? t('reservations.arrivalDate') : form.type === 'car' ? t('reservations.returnDate') : t('reservations.endDate')}
-            </label>
-            <CustomSelect
-              value={form.end_day_id}
-              onChange={value => set('end_day_id', value)}
-              placeholder={t('dayplan.dayN', { n: '?' })}
-              options={dayOptions}
-              size="sm"
-            />
-          </div>
-          <div style={{ flex: 1, minWidth: 0 }}>
-            <label className={labelClass}>
-              {form.type === 'flight' ? t('reservations.arrivalTime') : form.type === 'car' ? t('reservations.returnTime') : t('reservations.endTime')}
-            </label>
-            <CustomTimePicker value={form.arrival_time} onChange={v => set('arrival_time', v)} />
-          </div>
-          {form.type === 'flight' && toPick.airport && (
-            <div style={{ flex: 1, minWidth: 0 }}>
-              <label className={labelClass}>{t('reservations.meta.arrivalTimezone')}</label>
-              <div className={inputClass} style={{ padding: '8px 12px', color: 'var(--text-muted)', fontSize: 12, background: 'var(--bg-tertiary)' }}>
-                {toPick.airport.tz}
+            {/* Departure row */}
+            <div style={{ display: 'flex', gap: 8 }}>
+              <div style={{ flex: 1, minWidth: 0 }}>
+                <label className={labelClass}>{form.type === 'car' ? t('reservations.pickupDate') : t('reservations.date')}</label>
+                <CustomSelect value={form.start_day_id} onChange={value => set('start_day_id', value)} placeholder={t('dayplan.dayN', { n: '?' })} options={dayOptions} size="sm" />
+              </div>
+              <div style={{ flex: 1, minWidth: 0 }}>
+                <label className={labelClass}>{form.type === 'car' ? t('reservations.pickupTime') : t('reservations.startTime')}</label>
+                <CustomTimePicker value={form.departure_time} onChange={v => set('departure_time', v)} />
               </div>
             </div>
-          )}
-        </div>
 
-        {/* Flight-specific fields */}
-        {form.type === 'flight' && (
-          <div className="grid grid-cols-1 sm:grid-cols-2 gap-3">
-            <div>
-              <label className={labelClass}>{t('reservations.meta.airline')}</label>
-              <input type="text" value={form.meta_airline} onChange={e => set('meta_airline', e.target.value)}
-                placeholder="Lufthansa" className={inputClass} />
+            {/* Arrival row */}
+            <div style={{ display: 'flex', gap: 8 }}>
+              <div style={{ flex: 1, minWidth: 0 }}>
+                <label className={labelClass}>{form.type === 'car' ? t('reservations.returnDate') : t('reservations.endDate')}</label>
+                <CustomSelect value={form.end_day_id} onChange={value => set('end_day_id', value)} placeholder={t('dayplan.dayN', { n: '?' })} options={dayOptions} size="sm" />
+              </div>
+              <div style={{ flex: 1, minWidth: 0 }}>
+                <label className={labelClass}>{form.type === 'car' ? t('reservations.returnTime') : t('reservations.endTime')}</label>
+                <CustomTimePicker value={form.arrival_time} onChange={v => set('arrival_time', v)} />
+              </div>
             </div>
-            <div>
-              <label className={labelClass}>{t('reservations.meta.flightNumber')}</label>
-              <input type="text" value={form.meta_flight_number} onChange={e => set('meta_flight_number', e.target.value)}
-                placeholder="LH 123" className={inputClass} />
-            </div>
-          </div>
+          </>
         )}
 
         {/* Train-specific fields */}

client/src/components/Planner/usePlacesSidebar.ts

@@ -7,6 +7,7 @@ import { useContextMenu } from '../shared/ContextMenu'
 import { placesApi } from '../../api/client'
 import { useTripStore } from '../../store/tripStore'
 import { useCanDo } from '../../store/permissionsStore'
+import { useAuthStore } from '../../store/authStore'
 import type { Place, Category, Day, AssignmentsMap } from '../../types'
 
 export interface PlacesSidebarProps {
@@ -49,6 +50,8 @@ export function usePlacesSidebar(props: PlacesSidebarProps) {
   const loadTrip = useTripStore((s) => s.loadTrip)
   const can = useCanDo()
   const canEditPlaces = can('place_edit', trip)
+  // Places-API enrichment (#886) needs a Google Maps key; gate the toggle on it.
+  const canEnrichImport = useAuthStore((s) => s.hasMapsKey)
   const isNaverListImportEnabled = true
 
   const [fileImportOpen, setFileImportOpen] = useState(false)
@@ -94,6 +97,7 @@ export function usePlacesSidebar(props: PlacesSidebarProps) {
   const [listImportUrl, setListImportUrl] = useState('')
   const [listImportLoading, setListImportLoading] = useState(false)
   const [listImportProvider, setListImportProvider] = useState<'google' | 'naver'>('google')
+  const [listImportEnrich, setListImportEnrich] = useState(false)
   const availableListImportProviders: Array<'google' | 'naver'> = isNaverListImportEnabled ? ['google', 'naver'] : ['google']
   const hasMultipleListImportProviders = availableListImportProviders.length > 1
 
@@ -108,9 +112,10 @@ export function usePlacesSidebar(props: PlacesSidebarProps) {
     setListImportLoading(true)
     const provider = listImportProvider === 'naver' && isNaverListImportEnabled ? 'naver' : 'google'
     try {
+      const enrich = listImportEnrich && canEnrichImport
       const result = provider === 'google'
-        ? await placesApi.importGoogleList(tripId, listImportUrl.trim())
-        : await placesApi.importNaverList(tripId, listImportUrl.trim())
+        ? await placesApi.importGoogleList(tripId, listImportUrl.trim(), enrich)
+        : await placesApi.importNaverList(tripId, listImportUrl.trim(), enrich)
       await loadTrip(tripId)
       if (result.count === 0 && result.skipped > 0) {
         toast.warning(t('places.importAllSkipped'))
@@ -223,6 +228,7 @@ export function usePlacesSidebar(props: PlacesSidebarProps) {
     scrollContainerRef, onScrollTopChange,
     listImportOpen, setListImportOpen, listImportUrl, setListImportUrl,
     listImportLoading, listImportProvider, setListImportProvider,
+    listImportEnrich, setListImportEnrich, canEnrichImport,
     availableListImportProviders, hasMultipleListImportProviders, handleListImport,
     search, setSearch, filter, setFilter, categoryFilters, setCategoryFiltersLocal,
     selectMode, setSelectMode, selectedIds, setSelectedIds, pendingDeleteIds, setPendingDeleteIds,

client/src/components/Settings/AirTrailConnectionSection.tsx

@@ -0,0 +1,147 @@
+import React, { useEffect, useState } from 'react'
+import { Plane, Save } from 'lucide-react'
+import { useTranslation } from '../../i18n'
+import { useToast } from '../shared/Toast'
+import { airtrailApi } from '../../api/client'
+import Section from './Section'
+import ToggleSwitch from './ToggleSwitch'
+
+/**
+ * Settings → Integrations → AirTrail. Per-user connection to a self-hosted
+ * AirTrail instance (URL + Bearer API key). Mirrors the photo-provider (Immich)
+ * connection layout: stacked fields, a toggle, then Save / Test-connection with
+ * a status badge. The key is stored encrypted and never prefilled.
+ */
+export default function AirTrailConnectionSection(): React.ReactElement {
+  const { t } = useTranslation()
+  const toast = useToast()
+
+  const [url, setUrl] = useState('')
+  const [apiKey, setApiKey] = useState('')
+  const [allowInsecureTls, setAllowInsecureTls] = useState(false)
+  const [connected, setConnected] = useState(false)
+  const [loading, setLoading] = useState(true)
+  const [saving, setSaving] = useState(false)
+  const [testing, setTesting] = useState(false)
+
+  useEffect(() => {
+    airtrailApi
+      .getSettings()
+      .then(d => {
+        setUrl(d.url || '')
+        setAllowInsecureTls(!!d.allowInsecureTls)
+        setConnected(!!d.connected)
+      })
+      .catch(() => {})
+      .finally(() => setLoading(false))
+  }, [])
+
+  // Send the key only when the user typed a new one — never prefilled, so a blank
+  // field means "keep the stored key".
+  const keyPayload = (): { apiKey?: string } => {
+    const k = apiKey.trim()
+    return k ? { apiKey: k } : {}
+  }
+
+  const handleSave = async () => {
+    setSaving(true)
+    try {
+      const d = await airtrailApi.saveSettings({ url: url.trim(), allowInsecureTls, ...keyPayload() })
+      const status = await airtrailApi.status().catch(() => ({ connected: false }))
+      setConnected(!!status.connected)
+      setApiKey('')
+      if (d?.warning) toast.warning(d.warning)
+      else toast.success(t('settings.airtrail.toast.saved'))
+    } catch (err: any) {
+      toast.error(err?.response?.data?.error || t('settings.airtrail.toast.saveError'))
+    } finally {
+      setSaving(false)
+    }
+  }
+
+  const handleTest = async () => {
+    setTesting(true)
+    try {
+      const d = await airtrailApi.test({ url: url.trim(), allowInsecureTls, ...keyPayload() })
+      setConnected(!!d.connected)
+      if (d.connected) toast.success(t('settings.airtrail.test.success', { count: d.flightCount ?? 0 }))
+      else toast.error(d.error || t('settings.airtrail.test.failed'))
+    } catch {
+      toast.error(t('settings.airtrail.test.failed'))
+    } finally {
+      setTesting(false)
+    }
+  }
+
+  const canSave = !!url.trim() && (connected || !!apiKey.trim())
+
+  return (
+    <Section title={t('settings.airtrail.title')} icon={Plane}>
+      <div className="space-y-3">
+        <div>
+          <label className="block text-sm font-medium text-slate-700 mb-1.5">{t('settings.airtrail.url')}</label>
+          <input
+            type="url"
+            value={url}
+            onChange={e => setUrl(e.target.value)}
+            placeholder="https://airtrail.example.com"
+            className="w-full px-3 py-2.5 border border-slate-200 rounded-lg text-sm focus:outline-none focus:ring-2 focus:ring-slate-300"
+          />
+        </div>
+
+        <div>
+          <label className="block text-sm font-medium text-slate-700 mb-1.5">{t('settings.airtrail.apiKey')}</label>
+          <input
+            type="password"
+            value={apiKey}
+            onChange={e => setApiKey(e.target.value)}
+            autoComplete="off"
+            placeholder={connected && !apiKey ? '••••••••' : t('settings.airtrail.apiKeyPlaceholder')}
+            className="w-full px-3 py-2.5 border border-slate-200 rounded-lg text-sm focus:outline-none focus:ring-2 focus:ring-slate-300"
+          />
+          <p className="mt-1 text-xs text-slate-500">{t('settings.airtrail.apiKeyHint')}</p>
+        </div>
+
+        <div className="flex items-center gap-3">
+          <ToggleSwitch on={allowInsecureTls} onToggle={() => setAllowInsecureTls(v => !v)} />
+          <span className="text-sm font-medium text-slate-700">{t('settings.airtrail.allowInsecureTls')}</span>
+        </div>
+
+        <div className="flex flex-wrap items-center gap-3">
+          <button
+            onClick={handleSave}
+            disabled={saving || loading || !canSave}
+            className="flex items-center gap-2 px-4 py-2 bg-slate-900 text-white rounded-lg text-sm hover:bg-slate-700 disabled:bg-slate-400"
+          >
+            <Save className="w-4 h-4" /> {t('common.save')}
+          </button>
+          <button
+            onClick={handleTest}
+            disabled={testing || loading || !url.trim()}
+            className="flex items-center gap-2 px-4 py-2 border border-slate-200 rounded-lg text-sm hover:bg-slate-50"
+          >
+            {testing ? (
+              <div className="w-4 h-4 border-2 border-slate-300 border-t-slate-700 rounded-full animate-spin" />
+            ) : (
+              <Plane className="w-4 h-4" />
+            )}
+            {t('settings.airtrail.test.button')}
+          </button>
+          {connected ? (
+            <span className="basis-full sm:basis-auto text-xs font-medium text-green-600 flex items-center gap-1">
+              <span className="w-2 h-2 bg-green-500 rounded-full" />
+              {t('settings.airtrail.connected')}
+            </span>
+          ) : (
+            <span className="basis-full sm:basis-auto text-xs font-medium text-slate-400 flex items-center gap-1">
+              <span className="w-2 h-2 bg-slate-300 rounded-full" />
+              {t('settings.airtrail.notConnected')}
+            </span>
+          )}
+        </div>
+
+        <p className="text-xs text-slate-500">{t('settings.airtrail.hint')}</p>
+      </div>
+    </Section>
+  )
+}

client/src/components/Settings/DisplaySettingsTab.tsx

@@ -262,6 +262,37 @@ export default function DisplaySettingsTab(): React.ReactElement {
         <p className="text-xs mt-1 text-content-faint">{t('settings.bookingLabelsHint')}</p>
       </div>
 
+      {/* Explore places on the map (POI category pill) */}
+      <div>
+        <label className="block text-sm font-medium mb-2 text-content-secondary">{t('settings.mapPoiPill')}</label>
+        <div className="flex gap-3">
+          {[
+            { value: true, label: t('settings.on') || 'On' },
+            { value: false, label: t('settings.off') || 'Off' },
+          ].map(opt => (
+            <button
+              key={String(opt.value)}
+              onClick={async () => {
+                try { await updateSetting('map_poi_pill_enabled', opt.value) }
+                catch (e: unknown) { toast.error(e instanceof Error ? e.message : t('common.error')) }
+              }}
+              style={{
+                display: 'flex', alignItems: 'center', gap: 8,
+                padding: '10px 20px', borderRadius: 10, cursor: 'pointer',
+                fontFamily: 'inherit', fontSize: 14, fontWeight: 500,
+                border: (settings.map_poi_pill_enabled !== false) === opt.value ? '2px solid var(--text-primary)' : '2px solid var(--border-primary)',
+                background: (settings.map_poi_pill_enabled !== false) === opt.value ? 'var(--bg-hover)' : 'var(--bg-card)',
+                color: 'var(--text-primary)',
+                transition: 'all 0.15s',
+              }}
+            >
+              {opt.label}
+            </button>
+          ))}
+        </div>
+        <p className="text-xs mt-1 text-content-faint">{t('settings.mapPoiPillHint')}</p>
+      </div>
+
       {/* Blur Booking Codes */}
       <div>
         <label className="block text-sm font-medium mb-2 text-content-secondary">{t('settings.blurBookingCodes')}</label>

client/src/components/Settings/IntegrationsTab.tsx

@@ -6,6 +6,7 @@ import { Trash2, Copy, Terminal, Plus, Check, KeyRound, ChevronDown, ChevronRigh
 import { authApi, oauthApi } from '../../api/client'
 import { useAddonStore } from '../../store/addonStore'
 import PhotoProvidersSection from './PhotoProvidersSection'
+import AirTrailConnectionSection from './AirTrailConnectionSection'
 import { ALL_SCOPES } from '../../api/oauthScopes'
 import ScopeGroupPicker from '../OAuth/ScopeGroupPicker'
 
@@ -97,6 +98,7 @@ export default function IntegrationsTab(): React.ReactElement {
   return (
     <>
       <PhotoProvidersSection />
+      {S.airtrailEnabled && <AirTrailConnectionSection />}
       {S.mcpEnabled && <IntegrationsMcpSection {...S} />}
       <McpTokenModals {...S} />
       <OAuthClientModals {...S} />
@@ -109,6 +111,7 @@ function useIntegrations() {
   const toast = useToast()
   const { isEnabled: addonEnabled, loadAddons } = useAddonStore()
   const mcpEnabled = addonEnabled('mcp')
+  const airtrailEnabled = addonEnabled('airtrail')
 
   useEffect(() => {
     loadAddons()
@@ -289,7 +292,7 @@ function useIntegrations() {
 
 
   return {
-    t, locale, toast, mcpEnabled, oauthClients, setOauthClients, oauthSessions, setOauthSessions, oauthCreateOpen, setOauthCreateOpen, oauthNewName, setOauthNewName, oauthNewUris, setOauthNewUris, oauthNewScopes, setOauthNewScopes, oauthCreating, oauthCreatedClient, setOauthCreatedClient, oauthDeleteId, setOauthDeleteId, oauthRevokeId, setOauthRevokeId, oauthRotateId, setOauthRotateId, oauthRotatedSecret, setOauthRotatedSecret, oauthRotating, oauthScopesExpanded, setOauthScopesExpanded, oauthIsMachine, setOauthIsMachine, activeMcpTab, setActiveMcpTab, configOpenOAuth, setConfigOpenOAuth, configOpenToken, setConfigOpenToken, mcpTokens, setMcpTokens, mcpModalOpen, setMcpModalOpen, mcpNewName, setMcpNewName, mcpCreatedToken, setMcpCreatedToken, mcpCreating, mcpDeleteId, setMcpDeleteId, copiedKey, mcpEndpoint, mcpJsonConfigOAuth, mcpJsonConfig, handleCreateMcpToken, handleDeleteMcpToken, handleCopy, handleCreateOAuthClient, handleDeleteOAuthClient, handleRotateSecret, handleRevokeSession,
+    t, locale, toast, mcpEnabled, airtrailEnabled, oauthClients, setOauthClients, oauthSessions, setOauthSessions, oauthCreateOpen, setOauthCreateOpen, oauthNewName, setOauthNewName, oauthNewUris, setOauthNewUris, oauthNewScopes, setOauthNewScopes, oauthCreating, oauthCreatedClient, setOauthCreatedClient, oauthDeleteId, setOauthDeleteId, oauthRevokeId, setOauthRevokeId, oauthRotateId, setOauthRotateId, oauthRotatedSecret, setOauthRotatedSecret, oauthRotating, oauthScopesExpanded, setOauthScopesExpanded, oauthIsMachine, setOauthIsMachine, activeMcpTab, setActiveMcpTab, configOpenOAuth, setConfigOpenOAuth, configOpenToken, setConfigOpenToken, mcpTokens, setMcpTokens, mcpModalOpen, setMcpModalOpen, mcpNewName, setMcpNewName, mcpCreatedToken, setMcpCreatedToken, mcpCreating, mcpDeleteId, setMcpDeleteId, copiedKey, mcpEndpoint, mcpJsonConfigOAuth, mcpJsonConfig, handleCreateMcpToken, handleDeleteMcpToken, handleCopy, handleCreateOAuthClient, handleDeleteOAuthClient, handleRotateSecret, handleRevokeSession,
   }
 }
 

client/src/components/Todo/TodoListPanel.tsx

@@ -277,6 +277,7 @@ function DetailPane({ item, tripId, categories, members, onClose }: {
   const [desc, setDesc] = useState(item.description || '')
   const [dueDate, setDueDate] = useState(item.due_date || '')
   const [category, setCategory] = useState(item.category || '')
+  const [addingCategory, setAddingCategoryInline] = useState(false)
   const [assignedUserId, setAssignedUserId] = useState<number | null>(item.assigned_user_id)
   const [priority, setPriority] = useState(item.priority || 0)
   const [saving, setSaving] = useState(false)
@@ -378,21 +379,52 @@ function DetailPane({ item, tripId, categories, members, onClose }: {
         {/* Category */}
         <div>
           <label className={labelClass}>{t('todo.detail.category')}</label>
-          <CustomSelect
-            value={category}
-            onChange={v => setCategory(String(v))}
-            options={[
-              { value: '', label: t('todo.noCategory') },
-              ...categories.map(c => ({
-                value: c,
-                label: c,
-                icon: <span style={{ width: 8, height: 8, borderRadius: '50%', background: katColor(c, categories), display: 'inline-block' }} />,
-              })),
-            ]}
-            placeholder={t('todo.noCategory')}
-            size="sm"
-            disabled={!canEdit}
-          />
+          {addingCategory ? (
+            <div style={{ display: 'flex', gap: 4 }}>
+              <input
+                autoFocus
+                value={category}
+                onChange={e => setCategory(e.target.value)}
+                onKeyDown={e => { if (e.key === 'Enter') setAddingCategoryInline(false); if (e.key === 'Escape') { setCategory(''); setAddingCategoryInline(false) } }}
+                placeholder={t('todo.newCategory')}
+                style={{ flex: 1, fontSize: 13, padding: '8px 10px', border: '1px solid var(--border-primary)', borderRadius: 8, background: 'var(--bg-primary)', color: 'var(--text-primary)', fontFamily: 'inherit', outline: 'none' }}
+              />
+              <button type="button" onClick={() => setAddingCategoryInline(false)}
+                style={{ background: 'var(--bg-hover)', border: '1px solid var(--border-primary)', borderRadius: 8, padding: '0 10px', cursor: 'pointer', color: 'var(--text-primary)' }}>
+                <Check size={14} />
+              </button>
+            </div>
+          ) : (
+            <div style={{ display: 'flex', gap: 4 }}>
+              <div style={{ flex: 1, minWidth: 0 }}>
+                <CustomSelect
+                  value={category}
+                  onChange={v => setCategory(String(v))}
+                  options={[
+                    { value: '', label: t('todo.noCategory') },
+                    ...categories.map(c => ({
+                      value: c, label: c,
+                      icon: <span style={{ width: 8, height: 8, borderRadius: '50%', background: katColor(c, categories), display: 'inline-block' }} />,
+                    })),
+                    ...(category && !categories.includes(category) ? [{
+                      value: category, label: `${category} (${t('todo.newCategoryLabel') || 'new'})`,
+                      icon: <span style={{ width: 8, height: 8, borderRadius: '50%', background: '#9ca3af', display: 'inline-block' }} />,
+                    }] : []),
+                  ]}
+                  placeholder={t('todo.noCategory')}
+                  size="sm"
+                  disabled={!canEdit}
+                />
+              </div>
+              {canEdit && (
+                <button type="button" onClick={() => { setCategory(''); setAddingCategoryInline(true) }}
+                  title={t('todo.newCategory')}
+                  style={{ background: 'var(--bg-hover)', border: '1px solid var(--border-primary)', borderRadius: 8, padding: '0 10px', cursor: 'pointer', color: 'var(--text-muted)', fontFamily: 'inherit' }}>
+                  <Plus size={14} />
+                </button>
+              )}
+            </div>
+          )}
         </div>
 
         {/* Due date */}

client/src/hooks/useAirtrailConnection.ts

@@ -0,0 +1,31 @@
+import { useEffect, useState } from 'react'
+import { airtrailApi } from '../api/client'
+import { useAddonStore } from '../store/addonStore'
+
+/**
+ * Resolves whether the current user can use AirTrail in a trip: the addon must
+ * be enabled globally AND the user must have a working connection. Drives the
+ * "AirTrail Import/Sync" button visibility in the Transport panel.
+ */
+export function useAirtrailConnection() {
+  const airtrailEnabled = useAddonStore(s => s.isEnabled('airtrail'))
+  const [connected, setConnected] = useState(false)
+  const [loading, setLoading] = useState(false)
+
+  useEffect(() => {
+    if (!airtrailEnabled) {
+      setConnected(false)
+      return
+    }
+    let cancelled = false
+    setLoading(true)
+    airtrailApi
+      .status()
+      .then(d => { if (!cancelled) setConnected(!!d.connected) })
+      .catch(() => { if (!cancelled) setConnected(false) })
+      .finally(() => { if (!cancelled) setLoading(false) })
+    return () => { cancelled = true }
+  }, [airtrailEnabled])
+
+  return { airtrailEnabled, connected, available: airtrailEnabled && connected, loading }
+}

client/src/hooks/useRouteCalculation.ts

@@ -53,29 +53,44 @@ export function useRouteCalculation(tripStore: TripStoreState, selectedDayId: nu
       return pos != null
     })
 
-    // Build a unified list of places + transports sorted by effective position,
-    // then derive segments by resetting whenever a transport appears — mirrors getMergedItems order.
-    type Entry = { kind: 'place'; lat: number; lng: number } | { kind: 'transport' }
-    const entries: (Entry & { pos: number })[] = [
+    // The departure/arrival coordinate of a transport, if its endpoints carry one.
+    const epLoc = (r: any, role: 'from' | 'to'): { lat: number; lng: number } | null => {
+      const e = (r.endpoints || []).find((x: any) => x.role === role)
+      return e && e.lat != null && e.lng != null ? { lat: e.lat, lng: e.lng } : null
+    }
+
+    // Build a unified list of places + transports sorted by effective position.
+    type Entry =
+      | { kind: 'place'; lat: number; lng: number; pos: number }
+      | { kind: 'transport'; from: { lat: number; lng: number } | null; to: { lat: number; lng: number } | null; pos: number }
+    const entries: Entry[] = [
       ...da.filter(a => a.place?.lat && a.place?.lng).map(a => ({
         kind: 'place' as const, lat: a.place.lat!, lng: a.place.lng!, pos: a.order_index,
       })),
       ...dayTransports.map(r => ({
         kind: 'transport' as const,
+        from: epLoc(r, 'from'),
+        to: epLoc(r, 'to'),
         pos: (r.day_positions?.[dayId] ?? r.day_positions?.[String(dayId)] ?? r.day_plan_position) as number,
       })),
     ].sort((a, b) => a.pos - b.pos)
 
-    // Group consecutive located places into runs, resetting whenever a transport
-    // appears (you don't drive between a flight's endpoints) — mirrors getMergedItems order.
+    // Group located places into driving runs.
+    // - A transport WITH a location anchors the route to its departure point (you
+    //   travel there), then breaks the run (you don't drive the flight/train); its
+    //   arrival point starts the next run.
+    // - A transport WITHOUT a location is ignored entirely — the places around it
+    //   connect directly, as if the booking weren't there.
     const runs: { lat: number; lng: number }[][] = []
     let currentRun: { lat: number; lng: number }[] = []
     for (const entry of entries) {
       if (entry.kind === 'place') {
         currentRun.push({ lat: entry.lat, lng: entry.lng })
-      } else {
+      } else if (entry.from || entry.to) {
+        if (entry.from) currentRun.push(entry.from)
         if (currentRun.length >= 2) runs.push(currentRun)
         currentRun = []
+        if (entry.to) currentRun.push(entry.to)
       }
     }
     if (currentRun.length >= 2) runs.push(currentRun)
@@ -120,7 +135,9 @@ export function useRouteCalculation(tripStore: TripStoreState, selectedDayId: nu
       .filter(r => TRANSPORT_TYPES.includes(r.type))
       .map(r => {
         const pos = r.day_positions?.[selectedDayId] ?? r.day_positions?.[String(selectedDayId)] ?? r.day_plan_position
-        return `${r.id}:${r.day_id ?? ''}:${r.end_day_id ?? ''}:${r.reservation_time ?? ''}:${pos ?? ''}`
+        // Include endpoints so adding/moving a departure/arrival location re-routes.
+        const eps = (r.endpoints || []).map(e => `${e.role}@${e.lat ?? ''},${e.lng ?? ''}`).join(';')
+        return `${r.id}:${r.day_id ?? ''}:${r.end_day_id ?? ''}:${r.reservation_time ?? ''}:${pos ?? ''}:${eps}`
       })
       .sort()
       .join('|')

client/src/index.css

@@ -35,6 +35,23 @@ body { height: 100%; overflow: auto; overscroll-behavior: none; -webkit-overflow
   color: var(--text-primary) !important;
 }
 
+/* Mapbox GL hover popup — the name/category/address card on marker hover.
+   Matches the Leaflet map's white hover tooltip. pointer-events:none so moving
+   onto the popup never steals the marker's mouseleave and causes flicker. */
+.trek-map-popup { pointer-events: none; }
+.trek-map-popup .mapboxgl-popup-content {
+  padding: 7px 10px;
+  border-radius: 10px;
+  background: #fff;
+  box-shadow: 0 2px 12px rgba(0, 0, 0, 0.16);
+}
+.trek-map-popup .mapboxgl-popup-tip {
+  border-top-color: #fff;
+  border-bottom-color: #fff;
+  border-left-color: #fff;
+  border-right-color: #fff;
+}
+
 .atlas-tooltip {
   background: rgba(10, 10, 20, 0.6) !important;
   backdrop-filter: blur(20px) saturate(180%) !important;

client/src/pages/DashboardPage.test.tsx

@@ -226,7 +226,7 @@ describe('DashboardPage', () => {
       await user.click(archiveButtons[0]);
 
       // Switch to the archive filter segment
-      await user.click(screen.getByText('Archive'));
+      await user.click(screen.getByText('Archived'));
 
       await waitFor(() => {
         expect(screen.getAllByText('Paris Adventure')[0]).toBeInTheDocument();
@@ -293,7 +293,7 @@ describe('DashboardPage', () => {
       });
 
       // Switch to the archive filter
-      await user.click(screen.getByText('Archive'));
+      await user.click(screen.getByText('Archived'));
 
       await waitFor(() => {
         expect(screen.getByText('Old Rome Trip')).toBeInTheDocument();
@@ -442,7 +442,7 @@ describe('DashboardPage', () => {
       });
 
       // Switch to the archive filter
-      await user.click(screen.getByText('Archive'));
+      await user.click(screen.getByText('Archived'));
 
       await waitFor(() => {
         expect(screen.getByText('Old Rome Trip')).toBeInTheDocument();
@@ -644,7 +644,7 @@ describe('DashboardPage', () => {
       });
 
       // Archive filter reveals the archived trip
-      await user.click(screen.getByText('Archive'));
+      await user.click(screen.getByText('Archived'));
       await waitFor(() => {
         expect(screen.getByText('Old Archived Trip')).toBeInTheDocument();
       });
@@ -687,7 +687,7 @@ describe('DashboardPage', () => {
         expect(screen.getAllByText('My Active Trip')[0]).toBeInTheDocument();
       });
 
-      await user.click(screen.getByText('Archive'));
+      await user.click(screen.getByText('Archived'));
 
       await waitFor(() => {
         expect(screen.getByText('Restored Trip')).toBeInTheDocument();

client/src/pages/DashboardPage.tsx

@@ -16,7 +16,7 @@ import {
 import {
   Plus, Edit2, Trash2, Archive, Copy, ArrowRight, MapPin,
   Plane, Hotel, Utensils, Clock, RefreshCw, ArrowRightLeft, Calendar,
-  LayoutGrid, List, SlidersHorizontal, Ticket, X,
+  LayoutGrid, List, Ticket, X,
 } from 'lucide-react'
 import '../styles/dashboard.css'
 
@@ -120,15 +120,12 @@ export default function DashboardPage(): React.ReactElement {
                 <div className="sec-tools">
                   <div className="seg">
                     <button className={tripFilter === 'planned' ? 'on' : ''} onClick={() => setTripFilter('planned')}>{t('dashboard.filter.planned')}</button>
-                    <button className={tripFilter === 'archive' ? 'on' : ''} onClick={() => setTripFilter('archive')}>{t('dashboard.archive')}</button>
+                    <button className={tripFilter === 'archive' ? 'on' : ''} onClick={() => setTripFilter('archive')}>{t('dashboard.archived')}</button>
                     <button className={tripFilter === 'completed' ? 'on' : ''} onClick={() => setTripFilter('completed')}>{t('dashboard.mobile.completed')}</button>
                   </div>
                   <button className="tool-action" aria-label={t('dashboard.aria.toggleView')} onClick={toggleViewMode} style={{ width: 38, height: 38, borderRadius: 11 }}>
                     {viewMode === 'grid' ? <List size={17} /> : <LayoutGrid size={17} />}
                   </button>
-                  <button className="tool-action" aria-label={t('dashboard.aria.filter')} style={{ width: 38, height: 38, borderRadius: 11 }}>
-                    <SlidersHorizontal size={17} />
-                  </button>
                 </div>
               </div>
 

client/src/pages/LoginPage.tsx

@@ -491,6 +491,7 @@ export default function LoginPage(): React.ReactElement {
                       onChange={(e: React.ChangeEvent<HTMLInputElement>) => setMfaCode(e.target.value.toUpperCase().slice(0, 24))}
                       placeholder="000000 or XXXX-XXXX"
                       required
+                      autoFocus
                       style={inputBase}
                       onFocus={(e: React.FocusEvent<HTMLInputElement>) => e.target.style.borderColor = '#111827'}
                       onBlur={(e: React.FocusEvent<HTMLInputElement>) => e.target.style.borderColor = '#e5e7eb'}

client/src/pages/TripPlannerPage.tsx

@@ -5,6 +5,7 @@ import { useTripStore } from '../store/tripStore'
 import { useCanDo } from '../store/permissionsStore'
 import { useSettingsStore } from '../store/settingsStore'
 import { MapViewAuto as MapView } from '../components/Map/MapViewAuto'
+import { MapCompassPill } from '../components/Map/MapCompassPill'
 import { getCached, fetchPhoto } from '../services/photoService'
 import DayPlanSidebar from '../components/Planner/DayPlanSidebar'
 import PlacesSidebar from '../components/Planner/PlacesSidebar'
@@ -17,6 +18,7 @@ import TripMembersModal from '../components/Trips/TripMembersModal'
 import { ReservationModal } from '../components/Planner/ReservationModal'
 import { TransportModal } from '../components/Planner/TransportModal'
 import BookingImportModal from '../components/Planner/BookingImportModal'
+import AirTrailImportModal from '../components/Planner/AirTrailImportModal'
 // MemoriesPanel moved to Journey addon
 import ReservationsPanel from '../components/Planner/ReservationsPanel'
 import PackingListPanel from '../components/Packing/PackingListPanel'
@@ -42,6 +44,8 @@ import { usePlannerHistory } from '../hooks/usePlannerHistory'
 import type { Accommodation, TripMember, Day, Place, Reservation, PackingItem, TodoItem } from '../types'
 import { ListTodo, Upload, Plus, Trash2, FolderPlus } from 'lucide-react'
 import { useTripPlanner } from './tripPlanner/useTripPlanner'
+import { usePoiExplore } from '../components/Map/usePoiExplore'
+import PoiCategoryPill from '../components/Map/PoiCategoryPill'
 
 function ListsContainer({ tripId, packingItems, todoItems }: { tripId: number; packingItems: PackingItem[]; todoItems: TodoItem[] }) {
   const [subTab, setSubTab] = useState<'packing' | 'todo'>(() => {
@@ -185,6 +189,7 @@ export default function TripPlannerPage(): React.ReactElement | null {
     showTripForm, setShowTripForm, showMembersModal, setShowMembersModal,
     showReservationModal, setShowReservationModal, editingReservation, setEditingReservation,
     showBookingImport, setShowBookingImport, bookingImportAvailable,
+    airTrailAvailable, showAirTrailImport, setShowAirTrailImport,
     bookingForAssignmentId, setBookingForAssignmentId,
     showTransportModal, setShowTransportModal, editingTransport, setEditingTransport,
     transportModalDayId, setTransportModalDayId,
@@ -195,14 +200,18 @@ export default function TripPlannerPage(): React.ReactElement | null {
     isMobile, mapCategoryFilter, setMapCategoryFilter, mapPlacesFilter, setMapPlacesFilter,
     expandedDayIds, setExpandedDayIds, mapPlaces,
     route, routeSegments, routeInfo, setRoute, setRouteInfo, updateRouteForDay,
-    handleSelectDay, handlePlaceClick, handleMarkerClick, handleMapClick, handleMapContextMenu,
+    handleSelectDay, handlePlaceClick, handleMarkerClick, handleMapClick, handleMapContextMenu, openAddPlaceFromPoi,
     handleSavePlace, handleDeletePlace, confirmDeletePlace, confirmDeletePlaces,
-    handleAssignToDay, handleRemoveAssignment, handleReorder, handleUpdateDayTitle,
+    handleAssignToDay, handleRemoveAssignment, handleReorder, handleReorderDays, handleAddDay, handleUpdateDayTitle,
     handleSaveReservation, handleSaveTransport, handleDeleteReservation,
     selectedPlace, dayOrderMap, dayPlaces,
     mapTileUrl, defaultCenter, defaultZoom, fontStyle, splashDone,
   } = useTripPlanner()
 
+  const poi = usePoiExplore()
+  const [glMap, setGlMap] = useState<import('mapbox-gl').Map | null>(null)
+  const poiPillEnabled = useSettingsStore(s => s.settings.map_poi_pill_enabled) !== false
+
   if (isLoading || !splashDone) {
     return (
       <div className="bg-surface" style={{
@@ -300,8 +309,20 @@ export default function TripPlannerPage(): React.ReactElement | null {
                 const r = reservations.find(x => x.id === rid)
                 if (r) setMapTransportDetail(r)
               }}
+              pois={poi.pois}
+              onPoiClick={openAddPlaceFromPoi}
+              onViewportChange={poi.onViewportChange}
+              onMapReady={setGlMap}
             />
 
+            {(poiPillEnabled || glMap) && (
+              <div className="hidden md:flex" style={{ position: 'absolute', top: 14, left: '50%', transform: 'translateX(-50%)', zIndex: 25, pointerEvents: 'none', alignItems: 'flex-start', gap: 8 }}>
+                {poiPillEnabled && (
+                  <PoiCategoryPill active={poi.active} onToggle={poi.toggle} loadingKeys={poi.loadingKeys} errorKeys={poi.errorKeys} moved={poi.moved} onSearchArea={poi.searchArea} />
+                )}
+                {glMap && <MapCompassPill map={glMap} />}
+              </div>
+            )}
 
             <div className="hidden md:block" style={{ position: 'absolute', left: 10, top: 10, bottom: 10, zIndex: 20 }}>
               <button onClick={() => setLeftCollapsed(c => !c)}
@@ -342,6 +363,8 @@ export default function TripPlannerPage(): React.ReactElement | null {
                   onSelectDay={handleSelectDay}
                   onPlaceClick={handlePlaceClick}
                   onReorder={handleReorder}
+                  onReorderDays={handleReorderDays}
+                  onAddDay={handleAddDay}
                   onUpdateDayTitle={handleUpdateDayTitle}
                   onAssignToDay={handleAssignToDay}
                   onRouteCalculated={(r) => { if (r) { setRoute([r.coordinates]); setRouteInfo(r) } else { setRoute(null); setRouteInfo(null) } }}
@@ -593,7 +616,7 @@ export default function TripPlannerPage(): React.ReactElement | null {
                   </div>
                   <div style={{ flex: 1, overflow: 'auto' }}>
                     {mobileSidebarOpen === 'left'
-                      ? <DayPlanSidebar tripId={tripId} trip={trip} days={days} places={places} categories={categories} assignments={assignments} selectedDayId={selectedDayId} selectedPlaceId={selectedPlaceId} selectedAssignmentId={selectedAssignmentId} onSelectDay={(id) => { handleSelectDay(id); setMobileSidebarOpen(null) }} onPlaceClick={(placeId, assignmentId) => { handlePlaceClick(placeId, assignmentId) }} onReorder={handleReorder} onUpdateDayTitle={handleUpdateDayTitle} onAssignToDay={handleAssignToDay} onRouteCalculated={(r) => { if (r) { setRoute([r.coordinates]); setRouteInfo(r) } }} reservations={reservations} visibleConnectionIds={visibleConnections} onToggleConnection={toggleConnection} onAddReservation={(dayId) => { setEditingReservation(null); tripActions.setSelectedDay(dayId); setShowReservationModal(true); setMobileSidebarOpen(null) }} onAddTransport={can('day_edit', trip) ? (dayId) => { setTransportModalDayId(dayId); setEditingTransport(null); setShowTransportModal(true); setMobileSidebarOpen(null) } : undefined} onAddPlace={() => { setEditingPlace(null); setShowPlaceForm(true); setMobileSidebarOpen(null) }} onDayDetail={(day) => { setShowDayDetail(day); setSelectedPlaceId(null); selectAssignment(null) }} onRemoveAssignment={handleRemoveAssignment} onEditPlace={(place, assignmentId) => { setEditingPlace(place); setEditingAssignmentId(assignmentId || null); setShowPlaceForm(true); setMobileSidebarOpen(null) }} onDeletePlace={(placeId) => handleDeletePlace(placeId)} accommodations={tripAccommodations} routeShown={routeShown} routeProfile={routeProfile} onToggleRoute={() => setRouteShown(v => !v)} onSetRouteProfile={setRouteProfile} onNavigateToFiles={() => { setMobileSidebarOpen(null); handleTabChange('dateien') }} onExpandedDaysChange={setExpandedDayIds} pushUndo={pushUndo} canUndo={canUndo} lastActionLabel={lastActionLabel} onUndo={handleUndo} onEditTransport={can('day_edit', trip) ? (reservation) => { setEditingTransport(reservation); setTransportModalDayId(reservation.day_id ?? null); setShowTransportModal(true); setMobileSidebarOpen(null) } : undefined} onEditReservation={can('reservation_edit', trip) ? (r) => { setEditingReservation(r); setShowReservationModal(true); setMobileSidebarOpen(null) } : undefined} initialScrollTop={mobilePlanScrollTopRef.current} onScrollTopChange={(top) => { mobilePlanScrollTopRef.current = top }} />
+                      ? <DayPlanSidebar tripId={tripId} trip={trip} days={days} places={places} categories={categories} assignments={assignments} selectedDayId={selectedDayId} selectedPlaceId={selectedPlaceId} selectedAssignmentId={selectedAssignmentId} onSelectDay={(id) => { handleSelectDay(id); setMobileSidebarOpen(null) }} onPlaceClick={(placeId, assignmentId) => { handlePlaceClick(placeId, assignmentId) }} onReorder={handleReorder} onReorderDays={handleReorderDays} onAddDay={handleAddDay} onUpdateDayTitle={handleUpdateDayTitle} onAssignToDay={handleAssignToDay} onRouteCalculated={(r) => { if (r) { setRoute([r.coordinates]); setRouteInfo(r) } }} reservations={reservations} visibleConnectionIds={visibleConnections} onToggleConnection={toggleConnection} onAddReservation={(dayId) => { setEditingReservation(null); tripActions.setSelectedDay(dayId); setShowReservationModal(true); setMobileSidebarOpen(null) }} onAddTransport={can('day_edit', trip) ? (dayId) => { setTransportModalDayId(dayId); setEditingTransport(null); setShowTransportModal(true); setMobileSidebarOpen(null) } : undefined} onAddPlace={() => { setEditingPlace(null); setShowPlaceForm(true); setMobileSidebarOpen(null) }} onDayDetail={(day) => { setShowDayDetail(day); setSelectedPlaceId(null); selectAssignment(null) }} onRemoveAssignment={handleRemoveAssignment} onEditPlace={(place, assignmentId) => { setEditingPlace(place); setEditingAssignmentId(assignmentId || null); setShowPlaceForm(true); setMobileSidebarOpen(null) }} onDeletePlace={(placeId) => handleDeletePlace(placeId)} accommodations={tripAccommodations} routeShown={routeShown} routeProfile={routeProfile} onToggleRoute={() => setRouteShown(v => !v)} onSetRouteProfile={setRouteProfile} onNavigateToFiles={() => { setMobileSidebarOpen(null); handleTabChange('dateien') }} onExpandedDaysChange={setExpandedDayIds} pushUndo={pushUndo} canUndo={canUndo} lastActionLabel={lastActionLabel} onUndo={handleUndo} onEditTransport={can('day_edit', trip) ? (reservation) => { setEditingTransport(reservation); setTransportModalDayId(reservation.day_id ?? null); setShowTransportModal(true); setMobileSidebarOpen(null) } : undefined} onEditReservation={can('reservation_edit', trip) ? (r) => { setEditingReservation(r); setShowReservationModal(true); setMobileSidebarOpen(null) } : undefined} initialScrollTop={mobilePlanScrollTopRef.current} onScrollTopChange={(top) => { mobilePlanScrollTopRef.current = top }} showRouteToolsWhenExpanded />
                       : <PlacesSidebar tripId={tripId} places={places} categories={categories} assignments={assignments} selectedDayId={selectedDayId} selectedPlaceId={selectedPlaceId} onPlaceClick={(placeId) => { handlePlaceClick(placeId); setMobileSidebarOpen(null) }} onAddPlace={() => { setEditingPlace(null); setShowPlaceForm(true); setMobileSidebarOpen(null) }} onAssignToDay={handleAssignToDay} onEditPlace={(place) => { setEditingPlace(place); setEditingAssignmentId(null); setShowPlaceForm(true); setMobileSidebarOpen(null) }} onDeletePlace={(placeId) => handleDeletePlace(placeId)} onBulkDeletePlaces={(ids) => setDeletePlaceIds(ids)} onBulkDeleteConfirm={(ids) => confirmDeletePlaces(ids)} days={days} isMobile onCategoryFilterChange={setMapCategoryFilter} onPlacesFilterChange={setMapPlacesFilter} pushUndo={pushUndo} initialScrollTop={mobilePlacesScrollTopRef.current} onScrollTopChange={(top) => { mobilePlacesScrollTopRef.current = top }} />
                     }
                   </div>
@@ -613,6 +636,8 @@ export default function TripPlannerPage(): React.ReactElement | null {
               assignments={assignments}
               files={files}
               onAdd={() => { setEditingTransport(null); setShowTransportModal(true) }}
+              onAirTrailImport={() => setShowAirTrailImport(true)}
+              airTrailAvailable={airTrailAvailable}
               onEdit={(r) => { setEditingTransport(r); setShowTransportModal(true) }}
               onDelete={handleDeleteReservation}
               onNavigateToFiles={() => handleTabChange('dateien')}
@@ -682,6 +707,7 @@ export default function TripPlannerPage(): React.ReactElement | null {
       <ReservationModal isOpen={showReservationModal} onClose={() => { setShowReservationModal(false); setEditingReservation(null); setBookingForAssignmentId(null) }} onSave={handleSaveReservation} reservation={editingReservation} days={days} places={places} assignments={assignments} selectedDayId={selectedDayId} files={files} onFileUpload={canUploadFiles ? (fd) => tripActions.addFile(tripId, fd) : undefined} onFileDelete={(id) => tripActions.deleteFile(tripId, id)} accommodations={tripAccommodations} defaultAssignmentId={bookingForAssignmentId} />
       {showTransportModal && <TransportModal isOpen={showTransportModal} onClose={() => { setShowTransportModal(false); setEditingTransport(null); setTransportModalDayId(null) }} onSave={handleSaveTransport} reservation={editingTransport} days={days} selectedDayId={transportModalDayId} files={files} onFileUpload={canUploadFiles ? (fd) => tripActions.addFile(tripId, fd) : undefined} onFileDelete={(id) => tripActions.deleteFile(tripId, id)} />}
       <BookingImportModal isOpen={showBookingImport} onClose={() => setShowBookingImport(false)} tripId={tripId} pushUndo={pushUndo} />
+      <AirTrailImportModal isOpen={showAirTrailImport} onClose={() => setShowAirTrailImport(false)} tripId={tripId} pushUndo={pushUndo} />
       <ConfirmDialog
         isOpen={!!deletePlaceId}
         onClose={() => setDeletePlaceId(null)}

client/src/pages/admin/AdminUserModals.tsx

@@ -2,7 +2,7 @@ import React from 'react'
 import { adminApi } from '../../api/client'
 import Modal from '../../components/shared/Modal'
 import CustomSelect from '../../components/shared/CustomSelect'
-import { CheckCircle, ArrowUpCircle, ExternalLink, RefreshCw, AlertTriangle, Fingerprint } from 'lucide-react'
+import { CheckCircle, ArrowUpCircle, ExternalLink, RefreshCw, AlertTriangle, Fingerprint, Eye, EyeOff } from 'lucide-react'
 import type { TranslationFn } from '../../types'
 import type { useAdmin } from './useAdmin'
 
@@ -22,6 +22,8 @@ export default function AdminUserModals({ admin, t }: AdminUserModalsProps): Rea
     showRotateJwtModal, setShowRotateJwtModal, rotatingJwt, setRotatingJwt,
     handleCreateUser, handleSaveUser,
   } = admin
+  const [showCreatePw, setShowCreatePw] = React.useState(false)
+  const [showEditPw, setShowEditPw] = React.useState(false)
 
   return (
     <>
@@ -71,13 +73,24 @@ export default function AdminUserModals({ admin, t }: AdminUserModalsProps): Rea
           </div>
           <div>
             <label className="block text-sm font-medium text-slate-700 mb-1.5">{t('common.password')} *</label>
-            <input
-              type="password"
-              value={createForm.password}
-              onChange={e => setCreateForm(f => ({ ...f, password: e.target.value }))}
-              placeholder={t('common.password')}
-              className="w-full px-3 py-2.5 border border-slate-300 rounded-lg text-slate-900 focus:ring-2 focus:ring-slate-400 focus:border-transparent text-sm"
-            />
+            <div className="relative">
+              <input
+                type={showCreatePw ? 'text' : 'password'}
+                value={createForm.password}
+                onChange={e => setCreateForm(f => ({ ...f, password: e.target.value }))}
+                placeholder={t('common.password')}
+                className="w-full px-3 py-2.5 pr-10 border border-slate-300 rounded-lg text-slate-900 focus:ring-2 focus:ring-slate-400 focus:border-transparent text-sm"
+              />
+              <button
+                type="button"
+                onClick={() => setShowCreatePw(v => !v)}
+                tabIndex={-1}
+                aria-label="Show or hide password"
+                className="absolute right-2 top-1/2 -translate-y-1/2 p-1 text-slate-400 hover:text-slate-600"
+              >
+                {showCreatePw ? <EyeOff size={16} /> : <Eye size={16} />}
+              </button>
+            </div>
           </div>
           <div>
             <label className="block text-sm font-medium text-slate-700 mb-1.5">{t('settings.role')}</label>
@@ -138,13 +151,24 @@ export default function AdminUserModals({ admin, t }: AdminUserModalsProps): Rea
             </div>
             <div>
               <label className="block text-sm font-medium text-slate-700 mb-1.5">{t('admin.newPassword')} <span className="text-slate-400 font-normal">({t('admin.newPasswordHint')})</span></label>
-              <input
-                type="password"
-                value={editForm.password}
-                onChange={e => setEditForm(f => ({ ...f, password: e.target.value }))}
-                placeholder={t('admin.newPasswordPlaceholder')}
-                className="w-full px-3 py-2.5 border border-slate-300 rounded-lg text-slate-900 focus:ring-2 focus:ring-slate-400 focus:border-transparent text-sm"
-              />
+              <div className="relative">
+                <input
+                  type={showEditPw ? 'text' : 'password'}
+                  value={editForm.password}
+                  onChange={e => setEditForm(f => ({ ...f, password: e.target.value }))}
+                  placeholder={t('admin.newPasswordPlaceholder')}
+                  className="w-full px-3 py-2.5 pr-10 border border-slate-300 rounded-lg text-slate-900 focus:ring-2 focus:ring-slate-400 focus:border-transparent text-sm"
+                />
+                <button
+                  type="button"
+                  onClick={() => setShowEditPw(v => !v)}
+                  tabIndex={-1}
+                  aria-label="Show or hide password"
+                  className="absolute right-2 top-1/2 -translate-y-1/2 p-1 text-slate-400 hover:text-slate-600"
+                >
+                  {showEditPw ? <EyeOff size={16} /> : <Eye size={16} />}
+                </button>
+              </div>
             </div>
             <div>
               <label className="block text-sm font-medium text-slate-700 mb-1.5">{t('settings.role')}</label>

client/src/pages/admin/AdminUsersTab.tsx

@@ -15,7 +15,7 @@ interface AdminUsersTabProps {
 // create-invite modal. Pure layout around the useAdmin hook — no logic of its own.
 export default function AdminUsersTab({ admin, t, locale }: AdminUsersTabProps): React.ReactElement {
   const {
-    serverTimezone, hour12, currentUser,
+    hour12, currentUser,
     users, isLoading,
     setShowCreateUser,
     invites, showCreateInvite, setShowCreateInvite, inviteForm, setInviteForm,
@@ -92,10 +92,10 @@ export default function AdminUsersTab({ admin, t, locale }: AdminUsersTabProps):
                       </span>
                     </td>
                     <td className="px-5 py-3 text-sm text-slate-500">
-                      {new Date(u.created_at).toLocaleDateString(locale, { timeZone: serverTimezone })}
+                      {new Date(u.created_at).toLocaleDateString(locale)}
                     </td>
                     <td className="px-5 py-3 text-sm text-slate-500">
-                      {u.last_login ? new Date(u.last_login).toLocaleDateString(locale, { day: 'numeric', month: 'short', hour: '2-digit', minute: '2-digit', hour12, timeZone: serverTimezone }) : '—'}
+                      {u.last_login ? new Date(u.last_login).toLocaleDateString(locale, { day: 'numeric', month: 'short', hour: '2-digit', minute: '2-digit', hour12 }) : '—'}
                     </td>
                     <td className="px-5 py-3">
                       <div className="flex items-center gap-2 justify-end">
@@ -162,7 +162,7 @@ export default function AdminUsersTab({ admin, t, locale }: AdminUsersTabProps):
                     </div>
                     <div className="text-xs text-slate-400 mt-0.5">
                       {inv.used_count}/{inv.max_uses === 0 ? '∞' : inv.max_uses} {t('admin.invite.uses')}
-                      {inv.expires_at && ` · ${t('admin.invite.expiresAt')} ${new Date(inv.expires_at).toLocaleDateString(locale, { timeZone: serverTimezone })}`}
+                      {inv.expires_at && ` · ${t('admin.invite.expiresAt')} ${new Date(inv.expires_at).toLocaleDateString(locale)}`}
                       {` · ${t('admin.invite.createdBy')} ${inv.created_by_name}`}
                     </div>
                   </div>

client/src/pages/settings/useSettings.ts

@@ -16,7 +16,8 @@ export function useSettings() {
 
   const memoriesEnabled = addonEnabled('memories')
   const mcpEnabled = addonEnabled('mcp')
-  const hasIntegrations = memoriesEnabled || mcpEnabled
+  const airtrailEnabled = addonEnabled('airtrail')
+  const hasIntegrations = memoriesEnabled || mcpEnabled || airtrailEnabled
 
   const [appVersion, setAppVersion] = useState<string | null>(null)
   const [activeTab, setActiveTab] = useState('display')

client/src/pages/tripPlanner/useTripPlanner.ts

@@ -7,7 +7,7 @@ import { getCached, fetchPhoto } from '../../services/photoService'
 import { useToast } from '../../components/shared/Toast'
 import { Map, Ticket, PackageCheck, Wallet, FolderOpen, Users, Train } from 'lucide-react'
 import { useTranslation } from '../../i18n'
-import { addonsApi, accommodationsApi, authApi, tripsApi, assignmentsApi, healthApi } from '../../api/client'
+import { addonsApi, accommodationsApi, authApi, tripsApi, assignmentsApi, healthApi, airtrailApi } from '../../api/client'
 import { accommodationRepo } from '../../repo/accommodationRepo'
 import { offlineDb } from '../../db/offlineDb'
 import { useAuthStore } from '../../store/authStore'
@@ -16,6 +16,7 @@ import { useTripWebSocket } from '../../hooks/useTripWebSocket'
 import { useRouteCalculation } from '../../hooks/useRouteCalculation'
 import { usePlaceSelection } from '../../hooks/usePlaceSelection'
 import { usePlannerHistory } from '../../hooks/usePlannerHistory'
+import { useAirtrailConnection } from '../../hooks/useAirtrailConnection'
 import type { Accommodation, TripMember, Day, Place, Reservation } from '../../types'
 
 /**
@@ -123,7 +124,7 @@ export function useTripPlanner() {
   const [dayDetailCollapsed, setDayDetailCollapsed] = useState(false)
   const [showPlaceForm, setShowPlaceForm] = useState<boolean>(false)
   const [editingPlace, setEditingPlace] = useState<Place | null>(null)
-  const [prefillCoords, setPrefillCoords] = useState<{ lat: number; lng: number; name?: string; address?: string } | null>(null)
+  const [prefillCoords, setPrefillCoords] = useState<{ lat: number; lng: number; name?: string; address?: string; website?: string; phone?: string; osm_id?: string } | null>(null)
   const [editingAssignmentId, setEditingAssignmentId] = useState<number | null>(null)
   const [searchParams, setSearchParams] = useSearchParams()
 
@@ -140,6 +141,18 @@ export function useTripPlanner() {
   const [editingReservation, setEditingReservation] = useState<Reservation | null>(null)
   const [showBookingImport, setShowBookingImport] = useState<boolean>(false)
   const [bookingImportAvailable, setBookingImportAvailable] = useState<boolean>(false)
+  const { available: airTrailAvailable } = useAirtrailConnection()
+  const [showAirTrailImport, setShowAirTrailImport] = useState<boolean>(false)
+  // Pull this user's AirTrail edits as soon as they open the trip, so changes
+  // made in AirTrail show up without waiting for the background poll.
+  const airtrailSyncedRef = useRef<number | null>(null)
+  useEffect(() => {
+    if (!airTrailAvailable || !tripId || airtrailSyncedRef.current === tripId) return
+    airtrailSyncedRef.current = tripId
+    airtrailApi.sync()
+      .then(r => { if (r && r.changed > 0) tripActions.loadReservations(tripId) })
+      .catch(() => {})
+  }, [airTrailAvailable, tripId, tripActions])
   const [bookingForAssignmentId, setBookingForAssignmentId] = useState<number | null>(null)
   const [showTransportModal, setShowTransportModal] = useState<boolean>(false)
   const [editingTransport, setEditingTransport] = useState<Reservation | null>(null)
@@ -356,6 +369,24 @@ export function useTripPlanner() {
     } catch { /* best effort */ }
   }, [language])
 
+  // Open the Add-Place form pre-filled from an OSM "explore" POI marker — all the
+  // data already comes from the POI, so no reverse-geocode is needed.
+  const openAddPlaceFromPoi = useCallback((poi: { lat: number; lng: number; name: string; address: string | null; website: string | null; phone: string | null; osm_id: string }) => {
+    if (!can('place_edit', trip)) return
+    setPrefillCoords({
+      lat: poi.lat,
+      lng: poi.lng,
+      name: poi.name,
+      address: poi.address || '',
+      website: poi.website || undefined,
+      phone: poi.phone || undefined,
+      osm_id: poi.osm_id,
+    })
+    setEditingPlace(null)
+    setEditingAssignmentId(null)
+    setShowPlaceForm(true)
+  }, [trip])
+
   const handleSavePlace = useCallback(async (data) => {
     const pendingFiles = data._pendingFiles
     delete data._pendingFiles
@@ -523,6 +554,23 @@ export function useTripPlanner() {
     catch (err: unknown) { toast.error(err instanceof Error ? err.message : t('common.unknownError')) }
   }, [tripId, toast])
 
+  const handleReorderDays = useCallback((orderedIds: number[]) => {
+    const prevIds = (useTripStore.getState().days || [])
+      .slice().sort((a, b) => (a.day_number ?? 0) - (b.day_number ?? 0)).map(d => d.id)
+    tripActions.reorderDays(tripId, orderedIds)
+      .then(() => {
+        pushUndo(t('dayplan.reorderUndo'), async () => {
+          await tripActions.reorderDays(tripId, prevIds)
+        })
+      })
+      .catch(err => toast.error(err instanceof Error ? err.message : t('dayplan.reorderError')))
+  }, [tripId, toast, pushUndo])
+
+  const handleAddDay = useCallback((position?: number) => {
+    tripActions.insertDay(tripId, position)
+      .catch(err => toast.error(err instanceof Error ? err.message : t('dayplan.addDayError')))
+  }, [tripId, toast])
+
   const handleSaveReservation = async (data: Record<string, string | number | null> & { title: string }) => {
     try {
       if (editingReservation) {
@@ -631,6 +679,7 @@ export function useTripPlanner() {
     showTripForm, setShowTripForm, showMembersModal, setShowMembersModal,
     showReservationModal, setShowReservationModal, editingReservation, setEditingReservation,
     showBookingImport, setShowBookingImport, bookingImportAvailable,
+    airTrailAvailable, showAirTrailImport, setShowAirTrailImport,
     bookingForAssignmentId, setBookingForAssignmentId,
     showTransportModal, setShowTransportModal, editingTransport, setEditingTransport,
     transportModalDayId, setTransportModalDayId,
@@ -641,9 +690,9 @@ export function useTripPlanner() {
     isMobile, mapCategoryFilter, setMapCategoryFilter, mapPlacesFilter, setMapPlacesFilter,
     expandedDayIds, setExpandedDayIds, mapPlaces,
     route, routeSegments, routeInfo, setRoute, setRouteInfo, updateRouteForDay,
-    handleSelectDay, handlePlaceClick, handleMarkerClick, handleMapClick, handleMapContextMenu,
+    handleSelectDay, handlePlaceClick, handleMarkerClick, handleMapClick, handleMapContextMenu, openAddPlaceFromPoi,
     handleSavePlace, handleDeletePlace, confirmDeletePlace, confirmDeletePlaces,
-    handleAssignToDay, handleRemoveAssignment, handleReorder, handleUpdateDayTitle,
+    handleAssignToDay, handleRemoveAssignment, handleReorder, handleReorderDays, handleAddDay, handleUpdateDayTitle,
     handleSaveReservation, handleSaveTransport, handleDeleteReservation,
     selectedPlace, dayOrderMap, dayPlaces,
     mapTileUrl, defaultCenter, defaultZoom, fontStyle, splashDone,

client/src/store/settingsStore.ts

@@ -34,6 +34,7 @@ export const useSettingsStore = create<SettingsState>((set, get) => ({
     show_place_description: false,
     optimize_from_accommodation: true,
     map_provider: 'leaflet',
+    map_poi_pill_enabled: true,
     mapbox_access_token: '',
     mapbox_style: 'mapbox://styles/mapbox/standard',
     mapbox_3d_enabled: true,

client/src/store/slices/daysSlice.ts

@@ -0,0 +1,58 @@
+import { daysApi } from '../../api/client'
+import type { StoreApi } from 'zustand'
+import type { TripStoreState } from '../tripStore'
+import type { Day } from '../../types'
+import { getApiErrorMessage } from '../../types'
+
+type SetState = StoreApi<TripStoreState>['setState']
+type GetState = StoreApi<TripStoreState>['getState']
+
+export interface DaysSlice {
+  reorderDays: (tripId: number | string, orderedIds: number[]) => Promise<void>
+  insertDay: (tripId: number | string, position?: number) => Promise<Day | undefined>
+}
+
+export const createDaysSlice = (set: SetState, get: GetState): DaysSlice => ({
+  // Move whole days. Day rows stay stable (assignments/notes/bookings ride along
+  // by id); only positions change and, on a dated trip, dates stay pinned to
+  // their slots while the content moves across them. Optimistically reorder the
+  // list, then refresh to pull the server-side re-stamped dates + booking times.
+  reorderDays: async (tripId, orderedIds) => {
+    const prevDays = get().days
+    const byId = new Map(prevDays.map(d => [d.id, d]))
+    const sortedDates = prevDays.map(d => d.date).filter((d): d is string => !!d).sort()
+    const optimistic = orderedIds
+      .map((id, i) => {
+        const d = byId.get(id)
+        if (!d) return null
+        return { ...d, day_number: i + 1, date: sortedDates.length ? (sortedDates[i] ?? null) : d.date }
+      })
+      .filter((d): d is NonNullable<typeof d> => d !== null)
+
+    set({ days: optimistic })
+
+    try {
+      await daysApi.reorder(tripId, orderedIds)
+      await get().refreshDays(tripId)
+      await get().loadReservations(tripId)
+    } catch (err: unknown) {
+      set({ days: prevDays })
+      throw new Error(getApiErrorMessage(err, 'Error reordering days'))
+    }
+  },
+
+  // Insert a new empty day at a 1-based position (omit to append). On a dated
+  // trip this extends the trip by one day and re-pins dates server-side.
+  insertDay: async (tripId, position) => {
+    const prevDays = get().days
+    try {
+      const result = await daysApi.create(tripId, { position })
+      await get().refreshDays(tripId)
+      await get().loadReservations(tripId)
+      return result.day
+    } catch (err: unknown) {
+      set({ days: prevDays })
+      throw new Error(getApiErrorMessage(err, 'Error adding day'))
+    }
+  },
+})

client/src/store/slices/remoteEventHandler.ts

@@ -283,6 +283,15 @@ export function handleRemoteEvent(set: SetState, get: GetState, event: WebSocket
           dayNotes: newDayNotes,
         }
       }
+      case 'day:reordered': {
+        // Apply the new order instantly when we know all ids; the authoritative
+        // dates + re-stamped booking times are pulled by the refresh below.
+        const orderedIds = payload.orderedIds as number[] | undefined
+        if (!orderedIds || orderedIds.length !== state.days.length) return {}
+        const byId = new Map(state.days.map(d => [d.id, d]))
+        if (!orderedIds.every(id => byId.has(id))) return {}
+        return { days: orderedIds.map((id, i) => ({ ...byId.get(id)!, day_number: i + 1 })) }
+      }
 
       // Day Notes
       case 'dayNote:created': {
@@ -442,6 +451,16 @@ export function handleRemoteEvent(set: SetState, get: GetState, event: WebSocket
     }
   })
 
+  // A reorder/insert re-pins dates and re-stamps booking times server-side, so
+  // pull the authoritative days + reservations for collaborators.
+  if (type === 'day:reordered') {
+    const tripId = get().trip?.id
+    if (tripId) {
+      get().refreshDays(tripId)
+      get().loadReservations(tripId)
+    }
+  }
+
   // Write the change through to IndexedDB using the post-update state
   writeToDexie(type, payload as Record<string, unknown>, get())
 }

client/src/store/tripStore.ts

@@ -9,6 +9,7 @@ import { packingRepo } from '../repo/packingRepo'
 import { todoRepo } from '../repo/todoRepo'
 import { createPlacesSlice } from './slices/placesSlice'
 import { createAssignmentsSlice } from './slices/assignmentsSlice'
+import { createDaysSlice } from './slices/daysSlice'
 import { createDayNotesSlice } from './slices/dayNotesSlice'
 import { createPackingSlice } from './slices/packingSlice'
 import { createTodoSlice } from './slices/todoSlice'
@@ -24,6 +25,7 @@ import type {
 import { getApiErrorMessage } from '../types'
 import type { PlacesSlice } from './slices/placesSlice'
 import type { AssignmentsSlice } from './slices/assignmentsSlice'
+import type { DaysSlice } from './slices/daysSlice'
 import type { DayNotesSlice } from './slices/dayNotesSlice'
 import type { PackingSlice } from './slices/packingSlice'
 import type { TodoSlice } from './slices/todoSlice'
@@ -34,6 +36,7 @@ import type { FilesSlice } from './slices/filesSlice'
 export interface TripStoreState
   extends PlacesSlice,
     AssignmentsSlice,
+    DaysSlice,
     DayNotesSlice,
     PackingSlice,
     TodoSlice,
@@ -184,6 +187,7 @@ export const useTripStore = create<TripStoreState>((set, get) => ({
 
   ...createPlacesSlice(set, get),
   ...createAssignmentsSlice(set, get),
+  ...createDaysSlice(set, get),
   ...createDayNotesSlice(set, get),
   ...createPackingSlice(set, get),
   ...createTodoSlice(set, get),

client/src/styles/dashboard.css

@@ -378,8 +378,12 @@
 .trek-dash .trips.list-view { grid-template-columns: 1fr; gap: 12px; }
 .trek-dash .trips.list-view .trip-card { display: grid; grid-template-columns: 520px 1fr; gap: 0; height: auto; }
 .trek-dash .trips.list-view .trip-cover { border-radius: var(--r-lg) 0 0 var(--r-lg); height: 100px; aspect-ratio: unset; }
-.trek-dash .trips.list-view .trip-body { display: flex; align-items: center; justify-content: space-between; padding: 20px 32px; gap: 48px; }
-.trek-dash .trips.list-view .trip-meta { display: flex; gap: 32px; padding: 0; border: none; }
+.trek-dash .trips.list-view .trip-body { display: flex; align-items: center; justify-content: flex-end; padding: 16px 36px; gap: 28px; }
+/* Date rendered as a peer of the counts, set off by a vertical divider rather than
+   floating alone at the far left. */
+.trek-dash .trips.list-view .trip-dates { margin-bottom: 0; gap: 6px; }
+.trek-dash .trips.list-view .trip-dates .date-num { font-size: 15px; font-weight: 600; color: var(--ink); }
+.trek-dash .trips.list-view .trip-meta { display: flex; gap: 28px; padding: 0 0 0 28px; border: none; border-left: 1px solid var(--line); }
 .trek-dash .trip-card {
   position: relative; border-radius: var(--r-xl); overflow: hidden; background: var(--glass-bg);
   border: 1px solid var(--glass-border);
@@ -526,6 +530,9 @@
 
   /* Hero — immersive cover, title only (the pass is its own card below) */
   .trek-dash .hero-trip { height: 340px; margin-bottom: 16px; border-radius: var(--r-xl); }
+  /* No hover on touch — the lift/zoom just sticks after a tap and looks broken. */
+  .trek-dash .hero-trip:hover { transform: none; box-shadow: var(--sh-lg); }
+  .trek-dash .hero-trip:hover img.bg { transform: none; }
   .trek-dash .hero-content { padding: 18px; }
   /* the page already opens with the notification/profile strip, trim its top gap */
   .trek-dash .page { padding-top: 4px; }
@@ -580,25 +587,33 @@
   .trek-dash .trips { grid-template-columns: 1fr; gap: 16px; margin-bottom: 28px; }
   .trek-dash .add-trip-card { min-height: 180px; }
 
+  /* Touch devices have no hover — keep the edit/copy/archive/delete actions
+     visible at all times instead of revealing them on hover. */
+  .trek-dash .trip-actions { opacity: 1; }
+
   /* Compact list row on mobile — keeps the list view distinct from the grid. The
      desktop list row uses a 520px cover, which overflowed the phone width: the
      cover was clipped, the body pushed off-screen, and the fixed 100px cover
      height left a white strip beneath it. Use a fitting cover that stretches to
      the row, and show just the title + dates (the counts live in grid view and
      on the trip itself). */
-  .trek-dash .trips.list-view .trip-card { grid-template-columns: 42% 1fr; min-height: 92px; }
-  .trek-dash .trips.list-view .trip-cover { height: auto; aspect-ratio: unset; }
-  .trek-dash .trips.list-view .trip-cover-content { left: 14px; right: 14px; bottom: 12px; }
+  /* Mobile list row → stacked two-row: row 1 is a slim full-width cover banner
+     (image + title overlay + status top-left), row 2 is just the date, centred.
+     The counts stay grid-view-only on mobile. */
+  .trek-dash .trips.list-view .trip-card { grid-template-columns: 1fr; min-height: 0; }
+  .trek-dash .trips.list-view .trip-cover { height: 110px; aspect-ratio: unset; border-radius: 0; }
+  .trek-dash .trips.list-view .trip-cover-content { left: 16px; right: 16px; bottom: 11px; }
   .trek-dash .trips.list-view .trip-name {
-    font-size: 17px; overflow: hidden; text-overflow: ellipsis;
+    font-size: 18px; overflow: hidden; text-overflow: ellipsis;
     display: -webkit-box; -webkit-line-clamp: 2; -webkit-box-orient: vertical;
   }
-  .trek-dash .trips.list-view .trip-body { display: flex; align-items: center; justify-content: flex-start; padding: 12px 16px; }
-  .trek-dash .trips.list-view .trip-dates { margin-bottom: 0; justify-content: flex-start; }
+  .trek-dash .trips.list-view .trip-body { display: flex; align-items: center; justify-content: center; padding: 10px 16px; }
+  .trek-dash .trips.list-view .trip-dates { margin-bottom: 0; justify-content: center; font-size: 12.5px; }
+  .trek-dash .trips.list-view .trip-dates .date-num { font-size: 12.5px; }
   .trek-dash .trips.list-view .trip-meta { display: none; }
 
   /* Tools — stacked full-width cards (mockup) */
-  .trek-dash .page-sidebar { flex-direction: column; flex-wrap: nowrap; gap: 14px; margin: 0; padding: 0; }
+  .trek-dash .page-sidebar { flex-direction: column; flex-wrap: nowrap; gap: 14px; margin: 0 0 40px; padding: 0; }
   .trek-dash .page-sidebar .tool { flex: none; width: auto; }
 }
 

client/src/types.ts

@@ -113,6 +113,7 @@ export interface Settings {
   show_place_description: boolean
   blur_booking_codes?: boolean
   map_booking_labels?: boolean
+  map_poi_pill_enabled?: boolean
   optimize_from_accommodation?: boolean
   map_provider?: 'leaflet' | 'mapbox-gl'
   mapbox_access_token?: string

client/src/utils/dayMerge.test.ts

@@ -126,18 +126,18 @@ describe('getMergedItems', () => {
     expect(types).toEqual(['place', 'transport', 'place'])
   })
 
-  it('per-day position overrides time-based insertion', () => {
+  it('orders a timed transport chronologically regardless of a stale per-day position', () => {
     const dayAssignments = [
       { id: 1, order_index: 0, place: { place_time: '08:00' } },
       { id: 2, order_index: 1, place: { place_time: '13:00' } },
     ]
-    // Transport at 10:30 would normally go between the two places
-    // but per-day position 1.5 puts it after the second place
+    // The train is at 10:30, so it sorts between the 08:00 and 13:00 places by time —
+    // timed items are arranged chronologically even if an old manual position exists.
     const dayTransports = [
       { id: 20, type: 'train', day_id: 5, end_day_id: 5, reservation_time: '10:30', day_positions: { 5: 1.5 } },
     ]
     const result = getMergedItems({ dayAssignments, dayNotes: [], dayTransports, dayId: 5 })
     const types = result.map(i => i.type)
-    expect(types).toEqual(['place', 'place', 'transport'])
+    expect(types).toEqual(['place', 'transport', 'place'])
   })
 })

client/src/utils/dayMerge.ts

@@ -39,12 +39,66 @@ export function getDisplayTimeForDay(
   return r.reservation_time || null
 }
 
+/** Per-leg detail of a multi-leg flight, or null for single-leg / non-flight. */
+function parseFlightLegs(r: any): any[] | null {
+  if (r?.type !== 'flight') return null
+  let meta = r.metadata
+  if (typeof meta === 'string') { try { meta = JSON.parse(meta || '{}') } catch { meta = {} } }
+  // Defensive: recover metadata that was accidentally double-encoded by an earlier
+  // bug (a JSON string of a JSON string) so already-saved flights heal on read.
+  if (typeof meta === 'string') { try { meta = JSON.parse(meta || '{}') } catch { meta = {} } }
+  if (meta && Array.isArray(meta.legs) && meta.legs.length > 1) return meta.legs
+  return null
+}
+
+/**
+ * Expand a multi-leg flight into one synthetic reservation per leg that touches
+ * `dayId`, each with its own day span + departure/arrival time so it slots into
+ * the timeline independently. A single-leg flight (or any other reservation) is
+ * returned untouched, so existing behaviour is unchanged.
+ */
+export function expandFlightLegsForDay(
+  r: any,
+  dayId: number,
+  getDayOrder: (id: number) => number,
+  days: Array<{ id: number; date?: string | null }>
+): any[] {
+  const legs = parseFlightLegs(r)
+  if (!legs) return [r]
+  const dateOf = (id: number | null): string | null => (id == null ? null : (days.find(d => d.id === id)?.date ?? null))
+  const thisOrder = getDayOrder(dayId)
+  const out: any[] = []
+  legs.forEach((leg, i) => {
+    const dep = leg.dep_day_id ?? r.day_id ?? null
+    const arr = leg.arr_day_id ?? dep
+    if (dep == null) return
+    const depOrder = getDayOrder(dep)
+    const arrOrder = getDayOrder(arr ?? dep)
+    if (!(thisOrder >= depOrder && thisOrder <= arrOrder)) return
+    const depDate = dateOf(dep)
+    const arrDate = dateOf(arr ?? dep)
+    out.push({
+      ...r,
+      day_id: dep,
+      end_day_id: arr ?? dep,
+      reservation_time: leg.dep_time ? (depDate ? `${depDate}T${leg.dep_time}` : leg.dep_time) : null,
+      reservation_end_time: leg.arr_time ? (arrDate ? `${arrDate}T${leg.arr_time}` : leg.arr_time) : null,
+      // Each leg carries its OWN saved position (not the booking's) so items can be
+      // dropped between legs and persist; absent → falls back to time ordering.
+      day_positions: leg.day_positions || undefined,
+      day_plan_position: undefined,
+      __leg: { index: i, total: legs.length, from: leg.from ?? null, to: leg.to ?? null, airline: leg.airline ?? null, flight_number: leg.flight_number ?? null },
+    })
+  })
+  return out
+}
+
 /** Filter reservations that are active transports for the given day, excluding assignment-linked ones. */
 export function getTransportForDay(opts: {
   reservations: any[]
   dayId: number
   dayAssignmentIds: number[]
-  days: Array<{ id: number; day_number?: number }>
+  days: Array<{ id: number; day_number?: number; date?: string | null }>
 }): any[] {
   const { reservations, dayId, dayAssignmentIds, days } = opts
 
@@ -69,7 +123,34 @@ export function getTransportForDay(opts: {
       return thisDayOrder >= startOrder && thisDayOrder <= endOrder
     }
     return startDayId === dayId
-  })
+  }).flatMap(r => expandFlightLegsForDay(r, dayId, getDayOrder, days))
+}
+
+/**
+ * Order items chronologically: anything with a time (a place's place_time, a
+ * transport/leg display time, a timed note) sorts by that time. An item WITHOUT a
+ * time inherits the time of the timed item before it, so untimed items stay where
+ * they were manually placed. Stable on the incoming order for ties.
+ */
+function applyChronoOrder(
+  items: MergedItem[],
+  dayId: number,
+  getDisplayTime: (r: any, dayId: number) => string | null
+): MergedItem[] {
+  const timeOf = (it: MergedItem): number | null => {
+    if (it.type === 'place') return parseTimeToMinutes(it.data?.place?.place_time)
+    if (it.type === 'note') return parseTimeToMinutes(it.data?.time)
+    return parseTimeToMinutes(getDisplayTime(it.data, dayId))
+  }
+  let last = -Infinity
+  return items
+    .map((it, i) => {
+      const t = timeOf(it)
+      if (t != null) last = t
+      return { it, i, eff: t != null ? t : last }
+    })
+    .sort((a, b) => a.eff - b.eff || a.i - b.i)
+    .map(k => k.it)
 }
 
 /** Merge places, notes, and transports into a single ordered day timeline. */
@@ -94,9 +175,9 @@ export function getMergedItems(opts: {
     minutes: parseTimeToMinutes(getDisplayTime(r, dayId)) ?? 0,
   })).sort((a, b) => a.minutes - b.minutes)
 
-  if (timedTransports.length === 0) return baseItems
+  if (timedTransports.length === 0) return applyChronoOrder(baseItems, dayId, getDisplayTime)
   if (baseItems.length === 0) {
-    return timedTransports.map((item, i) => ({ type: item.type, sortKey: i, data: item.data }))
+    return applyChronoOrder(timedTransports.map((item, i) => ({ type: item.type, sortKey: i, data: item.data })), dayId, getDisplayTime)
   }
 
   // Insert transports among base items based on per-day position or time
@@ -132,5 +213,5 @@ export function getMergedItems(opts: {
     result.push({ type: timed.type, sortKey, data: timed.data })
   }
 
-  return result.sort((a, b) => a.sortKey - b.sortKey)
+  return applyChronoOrder(result.sort((a, b) => a.sortKey - b.sortKey), dayId, getDisplayTime)
 }

client/src/utils/flightLegs.ts

@@ -0,0 +1,105 @@
+// Multi-leg (layover) flight support.
+//
+// A flight booking is ONE reservation whose route is an ordered chain of airports
+// (e.g. FRA -> BER -> HND). The geometry + order are the source of truth in
+// `reservation.endpoints` (role 'from' for the first airport, 'stop' for each
+// intermediate one, 'to' for the last, ordered by `sequence`). The per-leg detail
+// — airline, flight number, and each segment's own day/time — lives in
+// `metadata.legs`. The top-level metadata (`departure_airport`/`arrival_airport`/
+// `airline`/`flight_number`) and `day_id`/`end_day_id` mirror the FIRST and LAST
+// leg so legacy readers keep working.
+//
+// A legacy single-leg flight (two endpoints, flat metadata, no `metadata.legs`)
+// is normalised here into a one-leg chain, so every renderer can use one path.
+
+import type { Reservation, ReservationEndpoint } from '../types'
+
+export interface FlightLeg {
+  from: string | null // IATA code (or null)
+  to: string | null
+  airline?: string
+  flight_number?: string
+  dep_day_id?: number | null
+  dep_time?: string | null // 'HH:mm'
+  arr_day_id?: number | null
+  arr_time?: string | null
+}
+
+/** reservation.metadata may be a JSON string or an already-parsed object. */
+export function parseReservationMetadata(r: Pick<Reservation, 'metadata'>): Record<string, any> {
+  const m = r.metadata
+  if (!m) return {}
+  if (typeof m === 'string') {
+    try {
+      let parsed = JSON.parse(m || '{}')
+      // Defensive: an earlier bug could double-encode metadata (a JSON string of a
+      // JSON string) — unwrap it once more so saved flights heal on read.
+      if (typeof parsed === 'string') { try { parsed = JSON.parse(parsed) } catch { /* keep */ } }
+      return (parsed && typeof parsed === 'object') ? parsed : {}
+    } catch { return {} }
+  }
+  return m as Record<string, any>
+}
+
+/** Endpoints ordered by `sequence` (geometry + order source of truth). */
+export function orderedEndpoints(r: Pick<Reservation, 'endpoints'>): ReservationEndpoint[] {
+  return (r.endpoints || []).slice().sort((a, b) => (a.sequence ?? 0) - (b.sequence ?? 0))
+}
+
+/**
+ * Ordered legs of a flight. `metadata.legs` is preferred; otherwise a single leg
+ * is derived from the endpoints (and finally the flat metadata) so that legacy
+ * single-leg flights — and flights created before this feature — still work.
+ */
+export function getFlightLegs(r: Reservation): FlightLeg[] {
+  const meta = parseReservationMetadata(r)
+  if (Array.isArray(meta.legs) && meta.legs.length > 0) {
+    return meta.legs.map((l: any): FlightLeg => ({
+      from: l.from ?? null,
+      to: l.to ?? null,
+      airline: l.airline || undefined,
+      flight_number: l.flight_number || undefined,
+      dep_day_id: l.dep_day_id ?? null,
+      dep_time: l.dep_time ?? null,
+      arr_day_id: l.arr_day_id ?? null,
+      arr_time: l.arr_time ?? null,
+    }))
+  }
+  // Legacy fallback: one leg from the endpoints / flat metadata.
+  const eps = orderedEndpoints(r)
+  const first = eps[0]
+  const last = eps[eps.length - 1]
+  const fromCode = first?.code ?? meta.departure_airport ?? null
+  const toCode = last?.code ?? meta.arrival_airport ?? null
+  if (!fromCode && !toCode) return []
+  return [{
+    from: fromCode,
+    to: toCode,
+    airline: meta.airline || undefined,
+    flight_number: meta.flight_number || undefined,
+    dep_day_id: r.day_id ?? null,
+    dep_time: first?.local_time ?? null,
+    arr_day_id: r.end_day_id ?? r.day_id ?? null,
+    arr_time: last?.local_time ?? null,
+  }]
+}
+
+/** Number of flight segments. 1 for a simple from -> to booking. */
+export function legCount(r: Reservation): number {
+  return getFlightLegs(r).length
+}
+
+export function isMultiLegFlight(r: Reservation): boolean {
+  return r.type === 'flight' && legCount(r) > 1
+}
+
+/**
+ * Ordered route labels (IATA codes, or names when no code) for display, e.g.
+ * ['FRA','BER','HND']. Uses endpoints; falls back to the flat metadata pair.
+ */
+export function routeStops(r: Reservation): string[] {
+  const eps = orderedEndpoints(r)
+  if (eps.length >= 2) return eps.map(e => e.code || e.name)
+  const meta = parseReservationMetadata(r)
+  return [meta.departure_airport, meta.arrival_airport].filter(Boolean) as string[]
+}

server/src/addons.ts

@@ -7,6 +7,7 @@ export const ADDON_IDS = {
   ATLAS: 'atlas',
   COLLAB: 'collab',
   JOURNEY: 'journey',
+  AIRTRAIL: 'airtrail',
 } as const;
 
 export type AddonId = typeof ADDON_IDS[keyof typeof ADDON_IDS];

server/src/db/migrations.ts

@@ -2460,6 +2460,35 @@ function runMigrations(db: Database.Database): void {
         if (after && after.region_code === row.region_code) del.run(row.id);
       }
     },
+    () => {
+      // AirTrail integration addon — disabled by default (opt-in). Per-user connection
+      // lives in Settings → Integrations; this row is only the admin-level global toggle.
+      try {
+        db.prepare("INSERT OR IGNORE INTO addons (id, name, description, type, icon, enabled, sort_order) VALUES (?, ?, ?, ?, ?, ?, ?)")
+          .run('airtrail', 'AirTrail', 'Sync flights from your self-hosted AirTrail instance', 'integration', 'Plane', 0, 14);
+      } catch (err: any) {
+        console.warn('[migrations] Non-fatal migration step failed:', err);
+      }
+    },
+    () => {
+      // AirTrail per-user connection (mirrors the Immich integration columns).
+      try { db.exec("ALTER TABLE users ADD COLUMN airtrail_url TEXT"); } catch (err: any) { if (!err.message?.includes('duplicate column name')) throw err; }
+      try { db.exec("ALTER TABLE users ADD COLUMN airtrail_api_key TEXT"); } catch (err: any) { if (!err.message?.includes('duplicate column name')) throw err; }
+      try { db.exec("ALTER TABLE users ADD COLUMN airtrail_allow_insecure_tls INTEGER DEFAULT 0"); } catch (err: any) { if (!err.message?.includes('duplicate column name')) throw err; }
+    },
+    () => {
+      // AirTrail flight linkage on reservations (#214) — lets a TREK transport
+      // remember its AirTrail origin so the two-way sync can match + update it.
+      // sync_enabled flips to 0 when the AirTrail flight is deleted (row kept).
+      try { db.exec("ALTER TABLE reservations ADD COLUMN external_source TEXT"); } catch (err: any) { if (!err.message?.includes('duplicate column name')) throw err; }
+      try { db.exec("ALTER TABLE reservations ADD COLUMN external_id TEXT"); } catch (err: any) { if (!err.message?.includes('duplicate column name')) throw err; }
+      try { db.exec("ALTER TABLE reservations ADD COLUMN external_owner_user_id INTEGER"); } catch (err: any) { if (!err.message?.includes('duplicate column name')) throw err; }
+      try { db.exec("ALTER TABLE reservations ADD COLUMN external_synced_at TEXT"); } catch (err: any) { if (!err.message?.includes('duplicate column name')) throw err; }
+      try { db.exec("ALTER TABLE reservations ADD COLUMN sync_enabled INTEGER DEFAULT 1"); } catch (err: any) { if (!err.message?.includes('duplicate column name')) throw err; }
+      try { db.exec("ALTER TABLE reservations ADD COLUMN external_hash TEXT"); } catch (err: any) { if (!err.message?.includes('duplicate column name')) throw err; }
+      // NULLs compare distinct in SQLite, so non-linked reservations don't collide.
+      db.exec("CREATE UNIQUE INDEX IF NOT EXISTS idx_reservations_external ON reservations(external_source, external_id, trip_id)");
+    },
   ];
 
   if (currentVersion < migrations.length) {

server/src/db/seeds.ts

@@ -98,6 +98,7 @@ function seedAddons(db: Database.Database): void {
       { id: 'naver_list_import', name: 'Naver List Import', description: 'Import places from shared Naver Maps lists', type: 'trip', icon: 'Link2', enabled: 1, sort_order: 13 },
       { id: 'collab', name: 'Collab', description: 'Notes, polls, and live chat for trip collaboration', type: 'trip', icon: 'Users', enabled: 1, sort_order: 6 },
       { id: 'journey', name: 'Journey', description: 'Trip tracking & travel journal — check-ins, photos, daily stories', type: 'global', icon: 'Compass', enabled: 0, sort_order: 35 },
+      { id: 'airtrail', name: 'AirTrail', description: 'Sync flights from your self-hosted AirTrail instance', type: 'integration', icon: 'Plane', enabled: 0, sort_order: 14 },
     ];
     const insertAddon = db.prepare('INSERT OR IGNORE INTO addons (id, name, description, type, icon, enabled, sort_order) VALUES (?, ?, ?, ?, ?, ?, ?)');
     for (const a of defaultAddons) insertAddon.run(a.id, a.name, a.description, a.type, a.icon, a.enabled, a.sort_order);

server/src/index.ts

@@ -79,6 +79,7 @@ const onListen = () => {
   scheduler.startDemoReset();
   scheduler.startIdempotencyCleanup();
   scheduler.startTrekPhotoCacheCleanup();
+  scheduler.startAirTrailSync();
   const { startTokenCleanup } = require('./services/ephemeralTokens');
   startTokenCleanup();
   import('./websocket').then(({ setupWebSocket }) => {

server/src/mcp/tools/trips.ts

@@ -78,10 +78,12 @@ export function registerTripTools(server: McpServer, userId: number, scopes: str
         start_date: z.string().regex(/^\d{4}-\d{2}-\d{2}$/).optional(),
         end_date: z.string().regex(/^\d{4}-\d{2}-\d{2}$/).optional(),
         currency: z.string().length(3).optional(),
+        is_archived: z.boolean().optional().describe('Archive (true) or unarchive (false) the trip'),
+        cover_image: z.string().optional().describe('Cover image path, e.g. /uploads/covers/abc.jpg'),
       },
       annotations: TOOL_ANNOTATIONS_WRITE,
     },
-    async ({ tripId, title, description, start_date, end_date, currency }) => {
+    async ({ tripId, title, description, start_date, end_date, currency, is_archived, cover_image }) => {
       if (isDemoUser(userId)) return demoDenied();
       if (!canAccessTrip(tripId, userId)) return noAccess();
       if (!hasTripPermission('trip_edit', tripId, userId)) return permissionDenied();
@@ -95,7 +97,7 @@ export function registerTripTools(server: McpServer, userId: number, scopes: str
         if (isNaN(d.getTime()) || d.toISOString().slice(0, 10) !== end_date)
           return { content: [{ type: 'text' as const, text: 'end_date is not a valid calendar date.' }], isError: true };
       }
-      const { updatedTrip } = updateTrip(tripId, userId, { title, description, start_date, end_date, currency }, 'user');
+      const { updatedTrip } = updateTrip(tripId, userId, { title, description, start_date, end_date, currency, is_archived, cover_image }, 'user');
       safeBroadcast(tripId, 'trip:updated', { trip: updatedTrip });
       return ok({ trip: updatedTrip });
     }

server/src/nest/app.module.ts

@@ -25,6 +25,7 @@ import { CollabModule } from './collab/collab.module';
 import { FilesModule } from './files/files.module';
 import { PhotosModule } from './photos/photos.module';
 import { MemoriesModule } from './memories/memories.module';
+import { AirtrailModule } from './integrations/airtrail.module';
 import { JourneyModule } from './journey/journey.module';
 import { ShareModule } from './share/share.module';
 import { SettingsModule } from './settings/settings.module';
@@ -41,10 +42,11 @@ import { IdempotencyInterceptor } from './common/idempotency.interceptor';
 
 /**
  * Root NestJS module for the incremental migration. Domain modules
- * (weather, notifications, ...) get registered here as they are migrated.
+ * (weather, notifications, integrations, ...) get registered here as they are
+ * migrated.
  */
 @Module({
-  imports: [DatabaseModule, WeatherModule, AirportsModule, ConfigModule, SystemNoticesModule, MapsModule, CategoriesModule, TagsModule, NotificationsModule, AtlasModule, VacayModule, PackingModule, TodoModule, BudgetModule, ReservationsModule, DaysModule, AssignmentsModule, PlacesModule, TripsModule, CollabModule, FilesModule, PhotosModule, MemoriesModule, JourneyModule, ShareModule, SettingsModule, BackupModule, AuthModule, OidcModule, OauthModule, AdminModule, AddonsModule, BookingImportModule],
+  imports: [DatabaseModule, WeatherModule, AirportsModule, ConfigModule, SystemNoticesModule, MapsModule, CategoriesModule, TagsModule, NotificationsModule, AtlasModule, VacayModule, PackingModule, TodoModule, BudgetModule, ReservationsModule, DaysModule, AssignmentsModule, PlacesModule, TripsModule, CollabModule, FilesModule, PhotosModule, MemoriesModule, AirtrailModule, JourneyModule, ShareModule, SettingsModule, BackupModule, AuthModule, OidcModule, OauthModule, AdminModule, AddonsModule, BookingImportModule],
   controllers: [HealthController],
   providers: [
     HealthService,

server/src/nest/booking-import/kitinerary-mapper.ts

@@ -90,6 +90,90 @@ function mapFlight(r: KiReservation, source: ParsedBookingItem['source']): Parse
   };
 }
 
+/** True when flight `b` is a short layover connection that continues flight `a`. */
+function sameConnection(a: KiReservation, b: KiReservation): boolean {
+  const fa = a.reservationFor as KiFlight | undefined;
+  const fb = b.reservationFor as KiFlight | undefined;
+  if (!fa || !fb) return false;
+  const arrIata = fa.arrivalAirport?.iataCode?.toUpperCase();
+  const depIata = fb.departureAirport?.iataCode?.toUpperCase();
+  if (!arrIata || !depIata || arrIata !== depIata) return false; // must connect at the same airport
+  const arrIso = toIsoString(fa.arrivalTime);
+  const depIso = toIsoString(fb.departureTime);
+  if (arrIso && depIso) {
+    const gapMs = new Date(depIso).getTime() - new Date(arrIso).getTime();
+    // A real layover is forward in time and short — anything longer (e.g. a
+    // round-trip return days later) stays a separate booking.
+    if (gapMs < 0 || gapMs > 24 * 3600 * 1000) return false;
+  }
+  return true;
+}
+
+/** Collapse several connecting flight legs (same PNR) into one multi-leg booking. */
+function mapFlightGroup(legs: KiReservation[], source: ParsedBookingItem['source']): ParsedBookingItem | null {
+  const flights = legs.map(l => l.reservationFor as KiFlight | undefined);
+  if (flights.some(f => !f)) return mapFlight(legs[0], source); // malformed → fall back to single
+  const fs = flights as KiFlight[];
+
+  const iataOf = (ap: KiFlight['departureAirport']) => ap?.iataCode?.toUpperCase() ?? null;
+  const makeEndpoint = (
+    ap: KiFlight['departureAirport'], role: 'from' | 'stop' | 'to', time: string | null, date: string | null,
+  ): ParsedEndpoint | null => {
+    const iata = iataOf(ap);
+    const found = iata ? findByIata(iata) : null;
+    const label = found ? (found.city ? `${found.city} (${found.iata})` : found.name) : (ap?.name ?? iata ?? 'Unknown');
+    if (found) return { role, sequence: 0, name: label, code: found.iata, lat: found.lat, lng: found.lng, timezone: found.tz, local_time: time, local_date: date };
+    const c = coords(ap?.geo);
+    if (c) return { role, sequence: 0, name: label, code: iata, lat: c.lat, lng: c.lng, timezone: null, local_time: time, local_date: date };
+    return null;
+  };
+
+  const endpoints: ParsedEndpoint[] = [];
+  const metaLegs: Record<string, unknown>[] = [];
+  const first = fs[0];
+  const firstDep = splitIso(first.departureTime);
+  const originEp = makeEndpoint(first.departureAirport, 'from', firstDep.time, firstDep.date);
+  if (originEp) endpoints.push(originEp);
+
+  fs.forEach((f, i) => {
+    const isLast = i === fs.length - 1;
+    const arr = splitIso(f.arrivalTime);
+    const arrEp = makeEndpoint(f.arrivalAirport, isLast ? 'to' : 'stop', arr.time, arr.date);
+    if (arrEp) endpoints.push(arrEp);
+    const airline = f.airline?.name ?? f.airline?.iataCode ?? '';
+    metaLegs.push({
+      from: iataOf(f.departureAirport),
+      to: iataOf(f.arrivalAirport),
+      ...(airline ? { airline } : {}),
+      ...(f.flightNumber ? { flight_number: f.flightNumber } : {}),
+      dep_time: splitIso(f.departureTime).time,
+      arr_time: arr.time,
+    });
+  });
+  endpoints.forEach((e, i) => { e.sequence = i; });
+
+  const last = fs[fs.length - 1];
+  const airline = first.airline?.name ?? first.airline?.iataCode ?? '';
+  const route = [iataOf(first.departureAirport), ...fs.map(f => iataOf(f.arrivalAirport))].filter(Boolean).join(' → ');
+  return {
+    type: 'flight',
+    title: airline ? `${airline} ${route}` : `Flight ${route}`,
+    reservation_time: toIsoString(first.departureTime),
+    reservation_end_time: toIsoString(last.arrivalTime),
+    confirmation_number: legs[0].reservationNumber ?? null,
+    metadata: {
+      ...(airline ? { airline } : {}),
+      ...(first.flightNumber ? { flight_number: first.flightNumber } : {}),
+      ...(iataOf(first.departureAirport) ? { departure_airport: iataOf(first.departureAirport) } : {}),
+      ...(iataOf(last.arrivalAirport) ? { arrival_airport: iataOf(last.arrivalAirport) } : {}),
+      legs: metaLegs,
+    },
+    endpoints,
+    needs_review: endpoints.length < fs.length + 1,
+    source,
+  };
+}
+
 function mapTrain(r: KiReservation, source: ParsedBookingItem['source']): ParsedBookingItem | null {
   const t = r.reservationFor as KiTrainTrip | undefined;
   if (!t) return null;
@@ -233,8 +317,25 @@ export function mapReservations(kiItems: KiReservation[], fileName: string): { i
     const source = { fileName, index: i };
     let item: ParsedBookingItem | null = null;
 
+    // Group consecutive connecting flight legs that share a PNR into one booking.
+    if (r['@type'] === 'FlightReservation') {
+      const pnr = r.reservationNumber ?? null;
+      const group = [r];
+      while (
+        i + 1 < kiItems.length &&
+        kiItems[i + 1]['@type'] === 'FlightReservation' &&
+        pnr != null &&
+        (kiItems[i + 1].reservationNumber ?? null) === pnr &&
+        sameConnection(group[group.length - 1], kiItems[i + 1])
+      ) {
+        group.push(kiItems[++i]);
+      }
+      item = group.length > 1 ? mapFlightGroup(group, source) : mapFlight(r, source);
+      if (item) items.push(item);
+      continue;
+    }
+
     switch (r['@type']) {
-      case 'FlightReservation':            item = mapFlight(r, source);  break;
       case 'TrainReservation':             item = mapTrain(r, source);   break;
       case 'BusReservation':              item = mapBus(r, source);     break;
       case 'BoatReservation':             item = mapBoat(r, source);    break;

server/src/nest/days/days.controller.ts

@@ -12,6 +12,7 @@ import {
 } from '@nestjs/common';
 import type { User } from '../../types';
 import { DaysService } from './days.service';
+import { DayReorderError } from '../../services/dayService';
 import { JwtAuthGuard } from '../auth/jwt-auth.guard';
 import { CurrentUser } from '../auth/current-user.decorator';
 
@@ -52,16 +53,47 @@ export class DaysController {
   create(
     @CurrentUser() user: User,
     @Param('tripId') tripId: string,
-    @Body() body: { date?: string; notes?: string },
+    @Body() body: { date?: string; notes?: string; position?: number },
     @Headers('x-socket-id') socketId?: string,
   ) {
     const trip = this.requireTrip(tripId, user);
     this.requireEdit(trip, user);
-    const day = this.days.create(tripId, body.date, body.notes);
-    this.days.broadcast(tripId, 'day:created', { day }, socketId);
+    // A `position` means "insert a new empty day here" (which on a dated trip
+    // extends the trip and re-pins dates); without it, the legacy append.
+    const day = body.position !== undefined
+      ? this.days.insert(tripId, body.position)
+      : this.days.create(tripId, body.date, body.notes);
+    // An insert can shuffle dates/positions of other days, so collaborators
+    // refetch the whole list; a plain append only needs the new day.
+    const event = body.position !== undefined ? 'day:reordered' : 'day:created';
+    this.days.broadcast(tripId, event, { day }, socketId);
     return { day };
   }
 
+  @Put('reorder')
+  reorder(
+    @CurrentUser() user: User,
+    @Param('tripId') tripId: string,
+    @Body() body: { orderedIds?: number[] },
+    @Headers('x-socket-id') socketId?: string,
+  ) {
+    const trip = this.requireTrip(tripId, user);
+    this.requireEdit(trip, user);
+    if (!Array.isArray(body.orderedIds)) {
+      throw new HttpException({ error: 'orderedIds must be an array' }, 400);
+    }
+    try {
+      this.days.reorder(tripId, body.orderedIds);
+    } catch (err) {
+      if (err instanceof DayReorderError) {
+        throw new HttpException({ error: err.message }, 400);
+      }
+      throw err;
+    }
+    this.days.broadcast(tripId, 'day:reordered', { orderedIds: body.orderedIds }, socketId);
+    return { success: true };
+  }
+
   @Put(':id')
   update(
     @CurrentUser() user: User,

server/src/nest/days/days.service.ts

@@ -39,6 +39,14 @@ export class DaysService {
     return dayService.createDay(tripId, date, notes);
   }
 
+  insert(tripId: string, position?: number) {
+    return dayService.insertDay(tripId, position);
+  }
+
+  reorder(tripId: string, orderedIds: number[]) {
+    return dayService.reorderDays(tripId, orderedIds);
+  }
+
   update(id: string, current: Parameters<typeof dayService.updateDay>[1], fields: { notes?: string; title?: string | null }) {
     return dayService.updateDay(id, current, fields);
   }

server/src/nest/integrations/airtrail-addon.guard.ts

@@ -0,0 +1,19 @@
+import { CanActivate, HttpException, Injectable } from '@nestjs/common';
+import { isAddonEnabled } from '../../services/adminService';
+import { ADDON_IDS } from '../../addons';
+
+/**
+ * Gates the AirTrail integration routes on the global `airtrail` addon. When the
+ * admin has it disabled the whole group answers 404. Declared before the
+ * JwtAuthGuard so the addon check wins over the 401 (same ordering as the
+ * Journey addon gate).
+ */
+@Injectable()
+export class AirtrailAddonGuard implements CanActivate {
+  canActivate(): boolean {
+    if (!isAddonEnabled(ADDON_IDS.AIRTRAIL)) {
+      throw new HttpException({ error: 'AirTrail addon is not enabled' }, 404);
+    }
+    return true;
+  }
+}

server/src/nest/integrations/airtrail-import.controller.ts

@@ -0,0 +1,42 @@
+import { Body, Controller, Headers, HttpException, Param, Post, UseGuards } from '@nestjs/common';
+import type { User } from '../../types';
+import { JwtAuthGuard } from '../auth/jwt-auth.guard';
+import { CurrentUser } from '../auth/current-user.decorator';
+import { ZodValidationPipe } from '../common/zod-validation.pipe';
+import { AirtrailAddonGuard } from './airtrail-addon.guard';
+import { airtrailImportSchema, type AirtrailImport, type AirtrailImportResult } from '@trek/shared';
+import { verifyTripAccess } from '../../services/tripAccess';
+import { checkPermission } from '../../services/permissions';
+import { importAirtrailFlights } from '../../services/airtrail/airtrailImport';
+
+/**
+ * POST /api/trips/:tripId/reservations/import/airtrail — turn selected AirTrail
+ * flights into reservations. Trip-scoped (reservation_edit) and addon-gated. The
+ * flights are re-fetched server-side with the caller's own key.
+ */
+@Controller('api/trips/:tripId/reservations/import')
+@UseGuards(AirtrailAddonGuard, JwtAuthGuard)
+export class AirtrailImportController {
+  private requireEdit(tripId: string, user: User): void {
+    const trip = verifyTripAccess(tripId, user.id);
+    if (!trip) throw new HttpException({ error: 'Trip not found' }, 404);
+    if (!checkPermission('reservation_edit', user.role, trip.user_id, user.id, trip.user_id !== user.id)) {
+      throw new HttpException({ error: 'No permission' }, 403);
+    }
+  }
+
+  @Post('airtrail')
+  async importAirtrail(
+    @CurrentUser() user: User,
+    @Param('tripId') tripId: string,
+    @Body(new ZodValidationPipe(airtrailImportSchema)) body: AirtrailImport,
+    @Headers('x-socket-id') socketId?: string,
+  ): Promise<AirtrailImportResult> {
+    this.requireEdit(tripId, user);
+    try {
+      return await importAirtrailFlights(tripId, user.id, body.flightIds, socketId);
+    } catch (err: any) {
+      throw new HttpException({ error: err?.message || 'AirTrail import failed' }, err?.status === 400 ? 400 : 502);
+    }
+  }
+}

server/src/nest/integrations/airtrail.controller.ts

@@ -0,0 +1,83 @@
+import { Body, Controller, Get, HttpCode, HttpException, Post, Put, Req, UseGuards } from '@nestjs/common';
+import type { Request } from 'express';
+import type { User } from '../../types';
+import { JwtAuthGuard } from '../auth/jwt-auth.guard';
+import { CurrentUser } from '../auth/current-user.decorator';
+import { ZodValidationPipe } from '../common/zod-validation.pipe';
+import { AirtrailAddonGuard } from './airtrail-addon.guard';
+import { getClientIp } from '../../services/auditLog';
+import { airtrailSettingsSchema, type AirtrailSettings } from '@trek/shared';
+import {
+  getConnectionSettings,
+  getConnectionStatus,
+  getFlightsForPicker,
+  saveSettings,
+  testConnection,
+} from '../../services/airtrail/airtrailService';
+import { runAirtrailSyncForUser } from '../../services/airtrail/airtrailSync';
+
+/**
+ * /api/integrations/airtrail — per-user AirTrail connection (#214).
+ *
+ * `status` and `test` answer 200 even on failure (the service shapes
+ * `{ connected: false, error }`); `settings` PUT validates with a 400. The API
+ * key is never echoed — `getSettings` returns it masked. The route group is
+ * gated on the `airtrail` addon (404 when disabled).
+ */
+@Controller('api/integrations/airtrail')
+@UseGuards(AirtrailAddonGuard, JwtAuthGuard)
+export class AirtrailController {
+  @Get('settings')
+  getSettings(@CurrentUser() user: User) {
+    return getConnectionSettings(user.id);
+  }
+
+  @Put('settings')
+  async putSettings(
+    @CurrentUser() user: User,
+    @Body(new ZodValidationPipe(airtrailSettingsSchema)) body: AirtrailSettings,
+    @Req() req: Request,
+  ) {
+    const result = await saveSettings(
+      user.id,
+      body.url,
+      body.apiKey,
+      !!body.allowInsecureTls,
+      getClientIp(req),
+    );
+    if (!result.success) {
+      throw new HttpException({ error: result.error }, 400);
+    }
+    return result.warning ? { success: true, warning: result.warning } : { success: true };
+  }
+
+  @Get('status')
+  getStatus(@CurrentUser() user: User) {
+    return getConnectionStatus(user.id);
+  }
+
+  @Get('flights')
+  async flights(@CurrentUser() user: User) {
+    try {
+      return { flights: await getFlightsForPicker(user.id) };
+    } catch (err: any) {
+      throw new HttpException({ error: err?.message || 'Could not load AirTrail flights' }, err?.status === 400 ? 400 : 502);
+    }
+  }
+
+  /** Pull this user's AirTrail edits into their linked reservations on demand. */
+  @Post('sync')
+  @HttpCode(200)
+  sync(@CurrentUser() user: User) {
+    return runAirtrailSyncForUser(user.id);
+  }
+
+  @Post('test')
+  @HttpCode(200)
+  test(
+    @CurrentUser() user: User,
+    @Body(new ZodValidationPipe(airtrailSettingsSchema)) body: AirtrailSettings,
+  ) {
+    return testConnection(user.id, body.url, body.apiKey, !!body.allowInsecureTls);
+  }
+}

server/src/nest/integrations/airtrail.module.ts

@@ -0,0 +1,14 @@
+import { Module } from '@nestjs/common';
+import { AirtrailController } from './airtrail.controller';
+import { AirtrailImportController } from './airtrail-import.controller';
+
+/**
+ * AirTrail integration domain. The connection lives under
+ * /api/integrations/airtrail; the flight import is trip-scoped under
+ * /api/trips/:tripId/reservations/import/airtrail. Business logic lives in
+ * services/airtrail/* (plain functions over better-sqlite3).
+ */
+@Module({
+  controllers: [AirtrailController, AirtrailImportController],
+})
+export class AirtrailModule {}

server/src/nest/maps/maps.controller.ts

@@ -55,18 +55,44 @@ export class MapsController {
     @CurrentUser() user: User,
     @Body('query') query: unknown,
     @Query('lang') lang?: string,
+    @Body('locationBias') locationBias?: { lat: number; lng: number; radius?: number },
   ): Promise<MapsSearchResult> {
     if (!query) {
       throw new HttpException({ error: 'Search query is required' }, 400);
     }
+    // Optional bias toward a coordinate (lat/lng[/radius]); improves foreign-region queries.
+    if (locationBias && !(Number.isFinite(locationBias.lat) && Number.isFinite(locationBias.lng))) {
+      throw new HttpException({ error: 'Invalid locationBias: lat and lng must be finite numbers' }, 400);
+    }
     try {
-      return await this.maps.search(user.id, query as string, lang);
+      return await this.maps.search(user.id, query as string, lang, locationBias);
     } catch (err: unknown) {
       console.error('Maps search error:', err);
       throw toHttpException(err, 'Search error', 500);
     }
   }
 
+  // OSM-only POI explore: places of a category within the current map viewport.
+  @Get('pois')
+  async pois(
+    @Query('category') category?: string,
+    @Query('south') south?: string,
+    @Query('west') west?: string,
+    @Query('north') north?: string,
+    @Query('east') east?: string,
+  ) {
+    if (!category) throw new HttpException({ error: 'A category is required' }, 400);
+    const bbox = { south: Number(south), west: Number(west), north: Number(north), east: Number(east) };
+    if (Object.values(bbox).some(v => !Number.isFinite(v))) {
+      throw new HttpException({ error: 'A valid bbox (south, west, north, east) is required' }, 400);
+    }
+    try {
+      return await this.maps.pois(category, bbox);
+    } catch (err: unknown) {
+      throw toHttpException(err, 'POI search error', 500);
+    }
+  }
+
   @Post('autocomplete')
   @HttpCode(200)
   async autocomplete(

server/src/nest/maps/maps.service.ts

@@ -16,6 +16,7 @@ import {
   getPlacePhoto,
   reverseGeocode,
   resolveGoogleMapsUrl,
+  searchOverpassPois,
 } from '../../services/mapsService';
 import { serveFilePath } from '../../services/placePhotoCache';
 
@@ -55,8 +56,8 @@ export class MapsService {
     return this.isSettingDisabled('places_photos_enabled');
   }
 
-  search(userId: number, query: string, lang?: string): Promise<MapsSearchResult> {
-    return searchPlaces(userId, query, lang) as Promise<MapsSearchResult>;
+  search(userId: number, query: string, lang?: string, locationBias?: { lat: number; lng: number; radius?: number }): Promise<MapsSearchResult> {
+    return searchPlaces(userId, query, lang, locationBias) as Promise<MapsSearchResult>;
   }
 
   autocomplete(userId: number, input: string, lang?: string, locationBias?: LocationBias): Promise<MapsAutocompleteResult> {
@@ -86,4 +87,9 @@ export class MapsService {
   resolveUrl(url: string): Promise<MapsResolveUrlResult> {
     return resolveGoogleMapsUrl(url) as Promise<MapsResolveUrlResult>;
   }
+
+  // OSM-only POI search by category within a viewport bbox (never calls Google).
+  pois(category: string, bbox: { south: number; west: number; north: number; east: number }) {
+    return searchOverpassPois(category, bbox);
+  }
 }

server/src/nest/places/places.controller.ts

@@ -163,27 +163,30 @@ export class PlacesController {
   }
 
   @Post('import/google-list')
-  async importGoogle(@CurrentUser() user: User, @Param('tripId') tripId: string, @Body('url') url: unknown, @Headers('x-socket-id') socketId?: string) {
-    return this.importList('google', user, tripId, url, socketId);
+  async importGoogle(@CurrentUser() user: User, @Param('tripId') tripId: string, @Body('url') url: unknown, @Body('enrich') enrich: unknown, @Headers('x-socket-id') socketId?: string) {
+    return this.importList('google', user, tripId, url, enrich, socketId);
   }
 
   @Post('import/naver-list')
-  async importNaver(@CurrentUser() user: User, @Param('tripId') tripId: string, @Body('url') url: unknown, @Headers('x-socket-id') socketId?: string) {
-    return this.importList('naver', user, tripId, url, socketId);
+  async importNaver(@CurrentUser() user: User, @Param('tripId') tripId: string, @Body('url') url: unknown, @Body('enrich') enrich: unknown, @Headers('x-socket-id') socketId?: string) {
+    return this.importList('naver', user, tripId, url, enrich, socketId);
   }
 
   /** Shared google/naver list import — identical flow, different provider + error string. */
-  private async importList(provider: 'google' | 'naver', user: User, tripId: string, url: unknown, socketId?: string) {
+  private async importList(provider: 'google' | 'naver', user: User, tripId: string, url: unknown, enrich: unknown, socketId?: string) {
     const trip = this.requireTrip(tripId, user);
     this.requireEdit(trip, user);
     if (!url || typeof url !== 'string') {
       throw new HttpException({ error: 'URL is required' }, 400);
     }
+    // Opt-in: re-resolve each imported place via the Places API to fill in
+    // photo / address / website / phone and persist a google_place_id (#886).
+    const opts = { enrich: parseBool(enrich, false), userId: user.id };
     const label = provider === 'google' ? 'Google' : 'Naver';
     try {
       const result = provider === 'google'
-        ? await this.places.importGoogleList(tripId, url)
-        : await this.places.importNaverList(tripId, url);
+        ? await this.places.importGoogleList(tripId, url, opts)
+        : await this.places.importNaverList(tripId, url, opts);
       if ('error' in result) {
         throw new HttpException({ error: result.error }, result.status);
       }

server/src/nest/places/places.service.ts

@@ -64,12 +64,12 @@ export class PlacesService {
     return svc.importMapFile(tripId, buffer, filename, opts);
   }
 
-  importGoogleList(tripId: string, url: string) {
-    return svc.importGoogleList(tripId, url);
+  importGoogleList(tripId: string, url: string, opts?: Parameters<typeof svc.importGoogleList>[2]) {
+    return svc.importGoogleList(tripId, url, opts);
   }
 
-  importNaverList(tripId: string, url: string) {
-    return svc.importNaverList(tripId, url);
+  importNaverList(tripId: string, url: string, opts?: Parameters<typeof svc.importNaverList>[2]) {
+    return svc.importNaverList(tripId, url, opts);
   }
 
   searchImage(tripId: string, id: string, userId: number) {

server/src/nest/reservations/reservations.controller.ts

@@ -14,6 +14,7 @@ import type { User } from '../../types';
 import { ReservationsService } from './reservations.service';
 import { JwtAuthGuard } from '../auth/jwt-auth.guard';
 import { CurrentUser } from '../auth/current-user.decorator';
+import { pushReservationToAirtrail } from '../../services/airtrail/airtrailSync';
 
 type ReservationBody = Record<string, unknown> & {
   title?: string;
@@ -115,6 +116,11 @@ export class ReservationsController {
     const cur = current as { title: string; type?: string };
     this.reservations.syncBudgetOnUpdate(tripId, id, body.title ?? '', body.type, cur.title, cur.type, body.create_budget_entry, socketId);
     this.reservations.broadcast(tripId, 'reservation:updated', { reservation }, socketId);
+    // Push a locally-edited AirTrail flight back to AirTrail (fire-and-forget,
+    // under the importer's credentials — see airtrailSync). #214
+    if ((reservation as any)?.external_source === 'airtrail' && (reservation as any)?.sync_enabled) {
+      void pushReservationToAirtrail(Number((reservation as any).id), Number(tripId)).catch(() => {});
+    }
     this.reservations.notifyBookingChange(tripId, user, body.title || cur.title, body.type || cur.type || '');
     return { reservation };
   }

server/src/scheduler.ts

@@ -334,6 +334,31 @@ function startTrekPhotoCacheCleanup(): void {
   });
 }
 
+// AirTrail sync: poll connected instances on an interval and reconcile linked
+// flights both ways (#214). The per-tick enable gate (addon + setting) lives in
+// runAirtrailSync, so toggling the addon takes effect without a restart.
+let airtrailSyncTask: ScheduledTask | null = null;
+
+function startAirTrailSync(): void {
+  if (airtrailSyncTask) { airtrailSyncTask.stop(); airtrailSyncTask = null; }
+
+  const { db } = require('./db/database');
+  const getSetting = (key: string) => (db.prepare('SELECT value FROM app_settings WHERE key = ?').get(key) as { value: string } | undefined)?.value;
+  const raw = parseInt(getSetting('airtrail_poll_interval_minutes') || '5', 10);
+  const minutes = Number.isFinite(raw) && raw >= 1 && raw <= 59 ? raw : 5;
+  const tz = process.env.TZ || 'UTC';
+  logInfo(`AirTrail sync: scheduled every ${minutes}m`);
+
+  airtrailSyncTask = cron.schedule(`*/${minutes} * * * *`, async () => {
+    try {
+      const { runAirtrailSync } = require('./services/airtrail/airtrailSync');
+      await runAirtrailSync();
+    } catch (err: unknown) {
+      logError(`AirTrail sync tick failed: ${err instanceof Error ? err.message : err}`);
+    }
+  }, { timezone: tz });
+}
+
 function stop(): void {
   if (currentTask) { currentTask.stop(); currentTask = null; }
   if (demoTask) { demoTask.stop(); demoTask = null; }
@@ -341,6 +366,7 @@ function stop(): void {
   if (versionCheckTask) { versionCheckTask.stop(); versionCheckTask = null; }
   if (idempotencyCleanupTask) { idempotencyCleanupTask.stop(); idempotencyCleanupTask = null; }
   if (trekPhotoCacheTask) { trekPhotoCacheTask.stop(); trekPhotoCacheTask = null; }
+  if (airtrailSyncTask) { airtrailSyncTask.stop(); airtrailSyncTask = null; }
 }
 
-export { start, stop, startDemoReset, startTripReminders, startTodoReminders, startVersionCheck, startIdempotencyCleanup, startTrekPhotoCacheCleanup, loadSettings, saveSettings, VALID_INTERVALS };
+export { start, stop, startDemoReset, startTripReminders, startTodoReminders, startVersionCheck, startIdempotencyCleanup, startTrekPhotoCacheCleanup, startAirTrailSync, loadSettings, saveSettings, VALID_INTERVALS };

server/src/services/airtrail/airtrailClient.ts

@@ -0,0 +1,197 @@
+import { safeFetch } from '../../utils/ssrfGuard';
+
+/**
+ * Thin HTTP client for the AirTrail REST API (github.com/johanohly/AirTrail).
+ * This is the ONLY place that talks to a user's AirTrail instance.
+ *
+ * Verified against AirTrail source:
+ *  - Auth: `Authorization: Bearer <key>`; a key maps to exactly one user.
+ *  - GET  /api/flight/list   — defaults to scope=mine. We NEVER send a scope
+ *    param so the key only ever returns its owner's own flights (isolation
+ *    holds even if an admin key is pasted).
+ *  - GET  /api/flight/get/{id}
+ *  - POST /api/flight/save   — `id` present => update, else create. seats[] is
+ *    required (>=1). A seat with userId '<USER_ID>' is attributed to the key
+ *    owner server-side, so we never need the caller's AirTrail user id.
+ *  - There is no webhook and no updated_at on a flight, so change detection is
+ *    snapshot-hash based (see airtrailSync).
+ */
+
+const TIMEOUT_MS = 12000;
+
+export interface AirtrailCreds {
+  /** Instance origin without a trailing /api. */
+  baseUrl: string;
+  apiKey: string;
+  allowInsecureTls: boolean;
+}
+
+export class AirtrailAuthError extends Error {
+  constructor(message = 'AirTrail rejected the API key') {
+    super(message);
+    this.name = 'AirtrailAuthError';
+  }
+}
+
+export class AirtrailRequestError extends Error {
+  status?: number;
+  constructor(message: string, status?: number) {
+    super(message);
+    this.name = 'AirtrailRequestError';
+    this.status = status;
+  }
+}
+
+export interface AirtrailAirport {
+  id: number;
+  icao: string | null;
+  iata: string | null;
+  name: string | null;
+  lat: number | null;
+  lon: number | null;
+  tz: string | null;
+  country: string | null;
+}
+
+export interface AirtrailSeat {
+  userId: string | null;
+  guestName: string | null;
+  seat: string | null;
+  seatNumber: string | null;
+  seatClass: string | null;
+}
+
+/** Airline/aircraft come back as joined objects (not bare codes) on a flight. */
+export interface AirtrailNamedCode {
+  id?: number;
+  icao?: string | null;
+  iata?: string | null;
+  name?: string | null;
+}
+
+/** A flight as returned by list/get (the fields TREK consumes). */
+export interface AirtrailFlightRaw {
+  id: number;
+  from: AirtrailAirport | null;
+  to: AirtrailAirport | null;
+  date: string | null;
+  datePrecision: string | null;
+  departure: string | null;
+  arrival: string | null;
+  airline: AirtrailNamedCode | null;
+  flightNumber: string | null;
+  aircraft: AirtrailNamedCode | null;
+  aircraftReg: string | null;
+  flightReason: string | null;
+  note: string | null;
+  seats: AirtrailSeat[];
+}
+
+/** Write shape accepted by POST /flight/save (airports/airline/aircraft as codes). */
+export interface AirtrailSavePayload {
+  id?: number;
+  from: string;
+  to: string;
+  departure: string;
+  departureTime?: string | null;
+  arrival?: string | null;
+  arrivalTime?: string | null;
+  datePrecision?: string;
+  airline?: string | null;
+  flightNumber?: string | null;
+  aircraft?: string | null;
+  aircraftReg?: string | null;
+  flightReason?: string | null;
+  note?: string | null;
+  seats: Array<{
+    userId: string | null;
+    guestName: string | null;
+    seat: string | null;
+    seatNumber: string | null;
+    seatClass: string | null;
+  }>;
+}
+
+function apiBase(baseUrl: string): string {
+  // Tolerate a pasted trailing slash or '/api' suffix so we never build '/api/api'.
+  const origin = baseUrl.trim().replace(/\/+$/, '').replace(/\/api$/i, '');
+  return origin + '/api';
+}
+
+/**
+ * Parse a response as JSON, but turn the cryptic "Unexpected token '<'" that a
+ * misconfigured URL produces (AirTrail serving its SPA / an auth-proxy login
+ * page) into an actionable message.
+ */
+async function parseJson<T>(resp: Response): Promise<T> {
+  const text = await resp.text();
+  try {
+    return JSON.parse(text) as T;
+  } catch {
+    throw new AirtrailRequestError(
+      'AirTrail returned a non-JSON response. Check the URL is your AirTrail base URL (e.g. https://airtrail.example.com, without /api) and that the instance is reachable without a separate login.',
+    );
+  }
+}
+
+async function request(creds: AirtrailCreds, path: string, init: RequestInit): Promise<Response> {
+  const url = apiBase(creds.baseUrl) + path;
+  let resp: Response;
+  try {
+    resp = await safeFetch(
+      url,
+      {
+        ...init,
+        headers: {
+          Authorization: `Bearer ${creds.apiKey}`,
+          Accept: 'application/json',
+          ...(init.headers || {}),
+        },
+        signal: AbortSignal.timeout(TIMEOUT_MS) as any,
+      },
+      { rejectUnauthorized: !creds.allowInsecureTls },
+    );
+  } catch (err: unknown) {
+    throw new AirtrailRequestError(err instanceof Error ? err.message : 'Could not reach AirTrail');
+  }
+  if (resp.status === 401 || resp.status === 403) {
+    throw new AirtrailAuthError();
+  }
+  return resp;
+}
+
+export async function listFlights(creds: AirtrailCreds): Promise<AirtrailFlightRaw[]> {
+  const resp = await request(creds, '/flight/list', { method: 'GET' });
+  if (!resp.ok) throw new AirtrailRequestError(`AirTrail list failed (HTTP ${resp.status})`, resp.status);
+  const data = await parseJson<{ flights?: AirtrailFlightRaw[] }>(resp);
+  return data.flights ?? [];
+}
+
+export async function getFlight(creds: AirtrailCreds, id: number): Promise<AirtrailFlightRaw | null> {
+  const resp = await request(creds, `/flight/get/${id}`, { method: 'GET' });
+  if (resp.status === 404) return null;
+  if (!resp.ok) throw new AirtrailRequestError(`AirTrail get failed (HTTP ${resp.status})`, resp.status);
+  const data = await parseJson<{ flight?: AirtrailFlightRaw }>(resp);
+  return data.flight ?? null;
+}
+
+export async function saveFlight(creds: AirtrailCreds, payload: AirtrailSavePayload): Promise<{ id?: number }> {
+  const resp = await request(creds, '/flight/save', {
+    method: 'POST',
+    headers: { 'Content-Type': 'application/json' },
+    body: JSON.stringify(payload),
+  });
+  if (!resp.ok) {
+    let msg = `AirTrail save failed (HTTP ${resp.status})`;
+    try {
+      const body = (await resp.json()) as { message?: string; errors?: unknown };
+      if (body?.message) msg = body.message;
+      else if (body?.errors) msg = JSON.stringify(body.errors);
+    } catch {
+      /* keep the generic message */
+    }
+    throw new AirtrailRequestError(msg, resp.status);
+  }
+  const data = await parseJson<{ id?: number }>(resp);
+  return { id: data.id };
+}

server/src/services/airtrail/airtrailImport.ts

@@ -0,0 +1,132 @@
+import type { AirtrailImportResult } from '@trek/shared';
+import { db } from '../../db/database';
+import { broadcast } from '../../websocket';
+import { createReservation } from '../reservationService';
+import { getAirtrailCredentials } from './airtrailService';
+import { AirtrailRequestError, listFlights } from './airtrailClient';
+import { canonicalHash, mapFlightToReservation } from './airtrailMapper';
+
+interface ExistingFlightRow {
+  id: number;
+  reservation_time: string | null;
+  metadata: string | null;
+  from_code: string | null;
+  to_code: string | null;
+}
+
+function depDate(t: string | null): string | null {
+  return t && /^\d{4}-\d{2}-\d{2}/.test(t) ? t.slice(0, 10) : null;
+}
+
+/** A loose "same physical flight" key: flight number + date, else route + date. */
+function softSignature(
+  date: string | null,
+  flightNumber: string | null,
+  fromCode: string | null,
+  toCode: string | null,
+): string | null {
+  if (!date) return null;
+  if (flightNumber) return `fn:${flightNumber.toUpperCase()}@${date}`;
+  if (fromCode && toCode) return `rt:${fromCode.toUpperCase()}-${toCode.toUpperCase()}@${date}`;
+  return null;
+}
+
+/**
+ * Import the given AirTrail flights into a trip as reservations (type:'flight'),
+ * recording the AirTrail linkage for two-way sync and broadcasting each one live.
+ *
+ * Dedup: a flight already linked to this trip is skipped ('already-imported'); a
+ * flight that looks like one already in the trip — e.g. the same flight another
+ * member already imported from their own AirTrail — is skipped ('already-in-trip').
+ * The server re-fetches the flights by id with the caller's own key, so the client
+ * cannot inject arbitrary flight data.
+ */
+export async function importAirtrailFlights(
+  tripId: string | number,
+  userId: number,
+  flightIds: string[],
+  socketId: string | undefined,
+): Promise<AirtrailImportResult> {
+  const creds = getAirtrailCredentials(userId);
+  if (!creds) throw new AirtrailRequestError('AirTrail is not connected', 400);
+
+  const wanted = new Set(flightIds.map(String));
+  const selected = (await listFlights(creds)).filter(f => wanted.has(String(f.id)));
+
+  const result: AirtrailImportResult = { imported: [], skipped: [] };
+
+  const linkedIds = new Set(
+    (db.prepare("SELECT external_id FROM reservations WHERE trip_id = ? AND external_source = 'airtrail'").all(tripId) as {
+      external_id: string | null;
+    }[])
+      .map(r => r.external_id)
+      .filter((v): v is string => !!v),
+  );
+
+  const existing = db
+    .prepare(
+      `SELECT r.id, r.reservation_time, r.metadata,
+              (SELECT code FROM reservation_endpoints WHERE reservation_id = r.id AND role = 'from' LIMIT 1) AS from_code,
+              (SELECT code FROM reservation_endpoints WHERE reservation_id = r.id AND role = 'to' LIMIT 1) AS to_code
+       FROM reservations r WHERE r.trip_id = ? AND r.type = 'flight'`,
+    )
+    .all(tripId) as ExistingFlightRow[];
+
+  const existingSigs = new Set<string>();
+  for (const row of existing) {
+    let fn: string | null = null;
+    try {
+      fn = row.metadata ? (JSON.parse(row.metadata).flight_number ?? null) : null;
+    } catch {
+      /* malformed metadata — ignore */
+    }
+    const sig = softSignature(depDate(row.reservation_time), fn, row.from_code, row.to_code);
+    if (sig) existingSigs.add(sig);
+  }
+
+  for (const flight of selected) {
+    const fid = String(flight.id);
+    if (linkedIds.has(fid)) {
+      result.skipped.push({ flightId: fid, reason: 'already-imported' });
+      continue;
+    }
+
+    const mapped = mapFlightToReservation(flight);
+    const sig = softSignature(
+      depDate(mapped.reservation_time),
+      (mapped.metadata.flight_number as string) ?? null,
+      mapped.endpoints.find(e => e.role === 'from')?.code ?? null,
+      mapped.endpoints.find(e => e.role === 'to')?.code ?? null,
+    );
+    if (sig && existingSigs.has(sig)) {
+      result.skipped.push({ flightId: fid, reason: 'already-in-trip', detail: mapped.title });
+      continue;
+    }
+
+    try {
+      const { reservation } = createReservation(tripId, mapped as any);
+      const now = new Date().toISOString();
+      db.prepare(
+        `UPDATE reservations SET external_source = 'airtrail', external_id = ?, external_owner_user_id = ?,
+                sync_enabled = 1, external_hash = ?, external_synced_at = ? WHERE id = ?`,
+      ).run(fid, userId, canonicalHash(flight), now, reservation.id);
+
+      // Carry the linkage on the broadcast payload so members see the badge live.
+      reservation.external_source = 'airtrail';
+      reservation.external_id = fid;
+      reservation.external_owner_user_id = userId;
+      reservation.sync_enabled = 1;
+      reservation.external_synced_at = now;
+
+      broadcast(tripId, 'reservation:created', { reservation }, socketId);
+      if (sig) existingSigs.add(sig);
+      linkedIds.add(fid);
+      result.imported.push(fid);
+    } catch (err) {
+      console.error('[airtrail-import] failed to import flight', fid, err instanceof Error ? err.message : err);
+      result.skipped.push({ flightId: fid, reason: 'invalid', detail: err instanceof Error ? err.message : undefined });
+    }
+  }
+
+  return result;
+}

server/src/services/airtrail/airtrailMapper.ts

@@ -0,0 +1,200 @@
+import * as crypto from 'node:crypto';
+import type { AirtrailAirport, AirtrailFlightRaw, AirtrailNamedCode } from './airtrailClient';
+import type { AirtrailFlight } from '@trek/shared';
+
+/** Preferred display/lookup code for an airport. */
+function airportCode(a: AirtrailAirport | null): string | null {
+  return a?.iata || a?.icao || null;
+}
+
+/**
+ * Airline/aircraft arrive as joined objects ({icao, iata, name, ...}); reduce
+ * them to a single code (ICAO preferred, matching AirTrail's save shape).
+ */
+function entityCode(e: AirtrailNamedCode | null | undefined): string | null {
+  return e?.icao || e?.iata || null;
+}
+
+/**
+ * Local calendar date + clock time for an instant at a given IANA zone.
+ * AirTrail stores `departure`/`arrival` as instants (ISO w/ offset) plus a local
+ * `date`; the airport-local wall time is what TREK shows and files days by.
+ */
+function localParts(iso: string | null, tz: string | null): { date: string | null; time: string | null } {
+  if (!iso) return { date: null, time: null };
+  try {
+    const d = new Date(iso);
+    if (isNaN(d.getTime())) return { date: null, time: null };
+    const fmt = new Intl.DateTimeFormat('en-CA', {
+      timeZone: tz || 'UTC',
+      year: 'numeric',
+      month: '2-digit',
+      day: '2-digit',
+      hour: '2-digit',
+      minute: '2-digit',
+      hour12: false,
+    });
+    const parts = fmt.formatToParts(d);
+    const get = (t: string) => parts.find(p => p.type === t)?.value ?? '';
+    const date = `${get('year')}-${get('month')}-${get('day')}`;
+    let hh = get('hour');
+    if (hh === '24') hh = '00'; // some ICU builds emit 24:00 for midnight
+    const time = `${hh}:${get('minute')}`;
+    return { date: /^\d{4}-\d{2}-\d{2}$/.test(date) ? date : null, time };
+  } catch {
+    return { date: null, time: null };
+  }
+}
+
+/** Raw AirTrail flight → the normalized shape the import picker consumes. */
+export function normalizeFlight(raw: AirtrailFlightRaw): AirtrailFlight {
+  return {
+    id: String(raw.id),
+    fromCode: airportCode(raw.from),
+    fromName: raw.from?.name ?? null,
+    toCode: airportCode(raw.to),
+    toName: raw.to?.name ?? null,
+    date: raw.date ?? null,
+    departure: raw.departure ?? null,
+    arrival: raw.arrival ?? null,
+    airline: entityCode(raw.airline),
+    flightNumber: raw.flightNumber ?? null,
+    aircraft: entityCode(raw.aircraft),
+    seatClass: (raw.seats?.find(s => s.userId) ?? raw.seats?.[0])?.seatClass ?? null,
+  };
+}
+
+export interface MappedEndpoint {
+  role: 'from' | 'to' | 'stop';
+  sequence: number;
+  name: string;
+  code: string | null;
+  lat: number;
+  lng: number;
+  timezone: string | null;
+  local_time: string | null;
+  local_date: string | null;
+}
+
+export interface MappedReservation {
+  title: string;
+  type: 'flight';
+  status: 'confirmed';
+  reservation_time: string | null;
+  reservation_end_time: string | null;
+  notes: string | null;
+  metadata: Record<string, unknown>;
+  endpoints: MappedEndpoint[];
+  needs_review: number;
+}
+
+function hasCoords(a: AirtrailAirport | null): a is AirtrailAirport & { lat: number; lng: number } {
+  return !!a && typeof a.lat === 'number' && typeof a.lon === 'number';
+}
+
+/** Raw AirTrail flight → the data createReservation() expects (type:'flight'). */
+export function mapFlightToReservation(raw: AirtrailFlightRaw): MappedReservation {
+  const dep = localParts(raw.departure, raw.from?.tz ?? null);
+  const arr = localParts(raw.arrival, raw.to?.tz ?? null);
+
+  const fromCode = airportCode(raw.from);
+  const toCode = airportCode(raw.to);
+  const datePrefix = raw.date || dep.date;
+  const reservation_time = datePrefix ? `${datePrefix}T${dep.time ?? '00:00'}` : null;
+  const reservation_end_time = arr.date ? `${arr.date}T${arr.time ?? '00:00'}` : null;
+
+  const endpoints: MappedEndpoint[] = [];
+  let needsReview = raw.datePrecision && raw.datePrecision !== 'day' ? 1 : 0;
+
+  if (hasCoords(raw.from)) {
+    endpoints.push({
+      role: 'from',
+      sequence: 0,
+      name: raw.from.name || fromCode || 'Departure',
+      code: fromCode,
+      lat: raw.from.lat,
+      lng: raw.from.lon,
+      timezone: raw.from.tz,
+      local_time: dep.time,
+      local_date: datePrefix,
+    });
+  } else {
+    needsReview = 1;
+  }
+
+  if (hasCoords(raw.to)) {
+    endpoints.push({
+      role: 'to',
+      sequence: 1,
+      name: raw.to.name || toCode || 'Arrival',
+      code: toCode,
+      lat: raw.to.lat,
+      lng: raw.to.lon,
+      timezone: raw.to.tz,
+      local_time: arr.time,
+      local_date: arr.date,
+    });
+  } else {
+    needsReview = 1;
+  }
+
+  const seat = raw.seats?.find(s => s.userId) ?? raw.seats?.[0];
+  const airlineCode = entityCode(raw.airline);
+  const aircraftCode = entityCode(raw.aircraft);
+  const metadata: Record<string, unknown> = {};
+  if (airlineCode) metadata.airline = airlineCode;
+  if (raw.flightNumber) metadata.flight_number = raw.flightNumber;
+  if (aircraftCode) metadata.aircraft = aircraftCode;
+  if (raw.aircraftReg) metadata.aircraft_reg = raw.aircraftReg;
+  if (raw.flightReason) metadata.flight_reason = raw.flightReason;
+  if (seat?.seatNumber || seat?.seatClass) metadata.seat = seat.seatNumber || seat.seatClass;
+
+  // The flight number already carries the airline prefix (e.g. "SAS983"), so it
+  // makes the clearest title; fall back to the route.
+  const title = raw.flightNumber?.trim() || `${fromCode || '?'} → ${toCode || '?'}`;
+
+  return {
+    title,
+    type: 'flight',
+    status: 'confirmed',
+    reservation_time,
+    reservation_end_time,
+    notes: raw.note ?? null,
+    metadata,
+    endpoints,
+    needs_review: needsReview,
+  };
+}
+
+/**
+ * Stable snapshot hash of an AirTrail flight, used by the sync engine to detect
+ * remote changes (AirTrail exposes no updated_at/etag) and to suppress TREK's own
+ * writes from re-triggering a pull. Only fields that can meaningfully change are
+ * included, in a fixed key order.
+ */
+export function canonicalHash(raw: AirtrailFlightRaw): string {
+  const snapshot = {
+    from: airportCode(raw.from),
+    to: airportCode(raw.to),
+    date: raw.date ?? null,
+    datePrecision: raw.datePrecision ?? 'day',
+    departure: raw.departure ?? null,
+    arrival: raw.arrival ?? null,
+    airline: entityCode(raw.airline),
+    flightNumber: raw.flightNumber ?? null,
+    aircraft: entityCode(raw.aircraft),
+    aircraftReg: raw.aircraftReg ?? null,
+    flightReason: raw.flightReason ?? null,
+    note: raw.note ?? null,
+    seats: (raw.seats ?? [])
+      .map(s => ({
+        userId: s.userId ?? null,
+        guestName: s.guestName ?? null,
+        seat: s.seat ?? null,
+        seatNumber: s.seatNumber ?? null,
+        seatClass: s.seatClass ?? null,
+      }))
+      .sort((a, b) => JSON.stringify(a).localeCompare(JSON.stringify(b))),
+  };
+  return crypto.createHash('sha256').update(JSON.stringify(snapshot)).digest('hex');
+}

server/src/services/airtrail/airtrailService.ts

@@ -0,0 +1,153 @@
+import type { AirtrailFlight } from '@trek/shared';
+import { db } from '../../db/database';
+import { maybe_encrypt_api_key, decrypt_api_key } from '../apiKeyCrypto';
+import { checkSsrf } from '../../utils/ssrfGuard';
+import { writeAudit } from '../auditLog';
+import { AirtrailAuthError, AirtrailCreds, AirtrailRequestError, listFlights } from './airtrailClient';
+import { normalizeFlight } from './airtrailMapper';
+
+const KEY_MASK = '••••••••';
+
+interface UserConnRow {
+  airtrail_url?: string | null;
+  airtrail_api_key?: string | null;
+  airtrail_allow_insecure_tls?: number | null;
+}
+
+function readRow(userId: number): UserConnRow | undefined {
+  return db
+    .prepare('SELECT airtrail_url, airtrail_api_key, airtrail_allow_insecure_tls FROM users WHERE id = ?')
+    .get(userId) as UserConnRow | undefined;
+}
+
+/** Decrypted creds for outbound calls, or null when the user has no connection. */
+export function getAirtrailCredentials(userId: number): AirtrailCreds | null {
+  const row = readRow(userId);
+  if (!row?.airtrail_url || !row?.airtrail_api_key) return null;
+  const apiKey = decrypt_api_key(row.airtrail_api_key);
+  if (!apiKey) return null;
+  return {
+    baseUrl: row.airtrail_url,
+    apiKey,
+    allowInsecureTls: !!row.airtrail_allow_insecure_tls,
+  };
+}
+
+/** Settings as shown in the UI — the key is never echoed, only masked. */
+export function getConnectionSettings(userId: number) {
+  const row = readRow(userId);
+  return {
+    url: row?.airtrail_url || '',
+    apiKeyMasked: row?.airtrail_api_key ? KEY_MASK : '',
+    allowInsecureTls: !!row?.airtrail_allow_insecure_tls,
+    connected: !!(row?.airtrail_url && row?.airtrail_api_key),
+  };
+}
+
+export async function saveSettings(
+  userId: number,
+  url: string | undefined,
+  apiKey: string | undefined,
+  allowInsecureTls: boolean,
+  clientIp: string | null,
+): Promise<{ success: boolean; warning?: string; error?: string }> {
+  const trimmedUrl = (url || '').trim();
+  let warning: string | undefined;
+
+  if (trimmedUrl) {
+    const ssrf = await checkSsrf(trimmedUrl);
+    // Reject only genuinely unusable URLs (malformed, unresolvable, non-http,
+    // loopback). Private/LAN instances are the common self-hosted case, so we
+    // persist them with a warning rather than blocking — the outbound calls
+    // still need ALLOW_INTERNAL_NETWORK=true to actually reach them.
+    if (!ssrf.allowed && !ssrf.isPrivate) {
+      return { success: false, error: ssrf.error ?? 'Invalid AirTrail URL' };
+    }
+    if (ssrf.isPrivate) {
+      writeAudit({
+        userId,
+        action: 'airtrail.private_ip_configured',
+        ip: clientIp,
+        details: { airtrail_url: trimmedUrl, resolved_ip: ssrf.resolvedIp },
+      });
+      warning = `AirTrail URL resolves to a private IP (${ssrf.resolvedIp}). Make sure this is intentional — the server may need ALLOW_INTERNAL_NETWORK=true to reach it.`;
+    }
+  }
+
+  // Only overwrite the stored key when a genuinely new value is supplied;
+  // a blank field or the mask means "keep the existing key".
+  const provided = (apiKey || '').trim();
+  const newKey = provided && provided !== KEY_MASK ? maybe_encrypt_api_key(provided) : undefined;
+
+  if (newKey !== undefined) {
+    db.prepare(
+      'UPDATE users SET airtrail_url = ?, airtrail_api_key = ?, airtrail_allow_insecure_tls = ? WHERE id = ?',
+    ).run(trimmedUrl || null, newKey, allowInsecureTls ? 1 : 0, userId);
+  } else {
+    db.prepare(
+      'UPDATE users SET airtrail_url = ?, airtrail_allow_insecure_tls = ? WHERE id = ?',
+    ).run(trimmedUrl || null, allowInsecureTls ? 1 : 0, userId);
+    // Clearing the URL with no key left makes the connection meaningless — drop the key too.
+    if (!trimmedUrl) {
+      db.prepare('UPDATE users SET airtrail_api_key = NULL WHERE id = ?').run(userId);
+    }
+  }
+
+  return { success: true, warning };
+}
+
+async function probe(creds: AirtrailCreds): Promise<{ connected: boolean; flightCount?: number; error?: string }> {
+  try {
+    const flights = await listFlights(creds);
+    return { connected: true, flightCount: flights.length };
+  } catch (err: unknown) {
+    if (err instanceof AirtrailAuthError) return { connected: false, error: 'Invalid API key' };
+    return { connected: false, error: err instanceof Error ? err.message : 'Connection failed' };
+  }
+}
+
+/** Live check using the stored connection. */
+export async function getConnectionStatus(
+  userId: number,
+): Promise<{ connected: boolean; flightCount?: number; error?: string }> {
+  const creds = getAirtrailCredentials(userId);
+  if (!creds) return { connected: false, error: 'Not configured' };
+  return probe(creds);
+}
+
+/**
+ * "Test connection" from the settings form. Uses the typed URL/key when given;
+ * falls back to the stored key when the key field still shows the mask.
+ */
+export async function testConnection(
+  userId: number,
+  url: string | undefined,
+  apiKey: string | undefined,
+  allowInsecureTls: boolean,
+): Promise<{ connected: boolean; flightCount?: number; error?: string }> {
+  const trimmedUrl = (url || '').trim();
+  const provided = (apiKey || '').trim();
+
+  const stored = getAirtrailCredentials(userId);
+  const effectiveUrl = trimmedUrl || stored?.baseUrl;
+  const effectiveKey = provided && provided !== KEY_MASK ? provided : stored?.apiKey;
+
+  if (!effectiveUrl || !effectiveKey) {
+    return { connected: false, error: 'URL and API key required' };
+  }
+
+  const ssrf = await checkSsrf(effectiveUrl);
+  if (!ssrf.allowed && !ssrf.isPrivate) {
+    return { connected: false, error: ssrf.error ?? 'Invalid AirTrail URL' };
+  }
+
+  return probe({ baseUrl: effectiveUrl, apiKey: effectiveKey, allowInsecureTls });
+}
+
+/** The user's AirTrail flights, normalized for the import picker. */
+export async function getFlightsForPicker(userId: number): Promise<AirtrailFlight[]> {
+  const creds = getAirtrailCredentials(userId);
+  if (!creds) throw new AirtrailRequestError('AirTrail is not connected', 400);
+  const raw = await listFlights(creds);
+  return raw.map(normalizeFlight);
+}

server/src/services/airtrail/airtrailSync.ts

@@ -0,0 +1,264 @@
+import { db } from '../../db/database';
+import { logError, logInfo } from '../auditLog';
+import { broadcast } from '../../websocket';
+import { isAddonEnabled } from '../adminService';
+import { ADDON_IDS } from '../../addons';
+import { getReservation, getReservationWithJoins, updateReservation } from '../reservationService';
+import { getAirtrailCredentials } from './airtrailService';
+import {
+  AirtrailAuthError,
+  AirtrailCreds,
+  AirtrailFlightRaw,
+  AirtrailSavePayload,
+  getFlight,
+  listFlights,
+  saveFlight,
+} from './airtrailClient';
+import { canonicalHash, mapFlightToReservation } from './airtrailMapper';
+
+/** Global on/off: the addon must be enabled and sync not explicitly turned off. */
+export function syncGloballyEnabled(): boolean {
+  if (!isAddonEnabled(ADDON_IDS.AIRTRAIL)) return false;
+  const row = db.prepare("SELECT value FROM app_settings WHERE key = 'airtrail_sync_enabled'").get() as
+    | { value: string }
+    | undefined;
+  return row?.value !== 'false';
+}
+
+function broadcastUpdated(tripId: number, reservationId: number): void {
+  try {
+    const reservation = getReservationWithJoins(reservationId);
+    if (reservation) broadcast(tripId, 'reservation:updated', { reservation });
+  } catch {
+    /* broadcast failure is non-fatal */
+  }
+}
+
+function detach(tripId: number, reservationId: number): void {
+  db.prepare('UPDATE reservations SET sync_enabled = 0 WHERE id = ?').run(reservationId);
+  broadcastUpdated(tripId, reservationId);
+}
+
+// ── AirTrail → TREK (poll) ───────────────────────────────────────────────────
+
+/**
+ * Reconcile one owner's linked reservations against their current AirTrail
+ * flights: apply field changes (detected by snapshot hash, since AirTrail has no
+ * updated_at) and, when a flight is gone from AirTrail, keep the TREK row but
+ * stop syncing it. Only already-imported flights are touched — new AirTrail
+ * flights are never auto-added to a trip. Returns how many rows changed.
+ */
+async function syncOwner(uid: number): Promise<number> {
+  const creds = getAirtrailCredentials(uid);
+  if (!creds) return 0; // owner disconnected — leave their linked rows as-is
+
+  let flights: AirtrailFlightRaw[];
+  try {
+    flights = await listFlights(creds);
+  } catch (err) {
+    if (err instanceof AirtrailAuthError) logError(`AirTrail sync: invalid API key for user ${uid}`);
+    return 0;
+  }
+  const byId = new Map(flights.map(f => [String(f.id), f]));
+
+  const linked = db
+    .prepare(
+      "SELECT id, trip_id, external_id, external_hash FROM reservations WHERE external_source = 'airtrail' AND sync_enabled = 1 AND external_owner_user_id = ?",
+    )
+    .all(uid) as { id: number; trip_id: number; external_id: string; external_hash: string | null }[];
+
+  let changed = 0;
+  for (const row of linked) {
+    const flight = byId.get(String(row.external_id));
+    if (!flight) {
+      detach(row.trip_id, row.id); // deleted in AirTrail → keep row, stop syncing
+      changed++;
+      continue;
+    }
+
+    const hash = canonicalHash(flight);
+    if (hash === row.external_hash) continue;
+
+    const current = getReservation(row.id, row.trip_id);
+    if (!current) continue;
+    try {
+      updateReservation(row.id, row.trip_id, mapFlightToReservation(flight) as any, current as any);
+      db.prepare('UPDATE reservations SET external_hash = ?, external_synced_at = ? WHERE id = ?').run(
+        hash,
+        new Date().toISOString(),
+        row.id,
+      );
+      broadcastUpdated(row.trip_id, row.id);
+      changed++;
+    } catch (err) {
+      logError(`AirTrail sync: failed to update reservation ${row.id}: ${err instanceof Error ? err.message : err}`);
+    }
+  }
+  return changed;
+}
+
+let running = false;
+
+/** Background poll across every connected owner (scheduler). */
+export async function runAirtrailSync(): Promise<void> {
+  if (running) return;
+  if (!syncGloballyEnabled()) return;
+  running = true;
+  let changed = 0;
+  try {
+    const owners = db
+      .prepare(
+        "SELECT DISTINCT external_owner_user_id AS uid FROM reservations WHERE external_source = 'airtrail' AND sync_enabled = 1 AND external_owner_user_id IS NOT NULL",
+      )
+      .all() as { uid: number }[];
+    for (const { uid } of owners) changed += await syncOwner(uid);
+    if (changed > 0) logInfo(`AirTrail sync: applied ${changed} change(s)`);
+  } catch (err) {
+    logError(`AirTrail sync failed: ${err instanceof Error ? err.message : err}`);
+  } finally {
+    running = false;
+  }
+}
+
+/**
+ * On-demand sync of just this user's linked flights — called when the user opens
+ * a trip so AirTrail-side edits show up immediately instead of waiting for the
+ * background poll.
+ */
+export async function runAirtrailSyncForUser(userId: number): Promise<{ changed: number }> {
+  if (!syncGloballyEnabled()) return { changed: 0 };
+  try {
+    return { changed: await syncOwner(userId) };
+  } catch (err) {
+    logError(`AirTrail sync (user ${userId}) failed: ${err instanceof Error ? err.message : err}`);
+    return { changed: 0 };
+  }
+}
+
+// ── TREK → AirTrail (push) ───────────────────────────────────────────────────
+
+function splitLocal(dt: string | null | undefined): { date: string | null; time: string | null } {
+  if (!dt) return { date: null, time: null };
+  const date = dt.slice(0, 10);
+  const m = dt.slice(10).match(/(\d{2}:\d{2})/);
+  return { date: /^\d{4}-\d{2}-\d{2}$/.test(date) ? date : null, time: m ? m[1] : null };
+}
+
+function buildSavePayload(reservation: any, existing: AirtrailFlightRaw): AirtrailSavePayload | null {
+  let meta: Record<string, any> = {};
+  try {
+    meta = reservation.metadata ? JSON.parse(reservation.metadata) : {};
+  } catch {
+    meta = {};
+  }
+  const endpoints: any[] = reservation.endpoints || [];
+  const fromEp = endpoints.find(e => e.role === 'from');
+  const toEp = endpoints.find(e => e.role === 'to');
+  const fromCode = fromEp?.code || existing.from?.iata || existing.from?.icao || null;
+  const toCode = toEp?.code || existing.to?.iata || existing.to?.icao || null;
+  if (!fromCode || !toCode) return null;
+
+  const dep = splitLocal(reservation.reservation_time);
+  const arr = splitLocal(reservation.reservation_end_time);
+  if (!dep.date) return null;
+
+  // Preserve the existing seat manifest (an update replaces all seats); fall back
+  // to the key-owner placeholder so AirTrail attributes it to the connecting user.
+  const seats = (existing.seats ?? []).map(s => ({
+    userId: s.userId,
+    guestName: s.guestName,
+    seat: s.seat,
+    seatNumber: s.seatNumber,
+    seatClass: s.seatClass,
+  }));
+  if (seats.length === 0) {
+    seats.push({ userId: '<USER_ID>', guestName: null, seat: null, seatNumber: null, seatClass: null });
+  }
+
+  // Push the seat the user set in TREK onto their own AirTrail seat (the one with
+  // a userId), leaving any co-passenger seats untouched.
+  const seatNumber = typeof meta.seat === 'string' && meta.seat.trim() ? meta.seat.trim() : null;
+  if (seatNumber) {
+    const ownSeat = seats.find(s => s.userId) ?? seats[0];
+    if (ownSeat) ownSeat.seatNumber = seatNumber;
+  }
+
+  return {
+    id: Number(reservation.external_id),
+    from: fromCode,
+    to: toCode,
+    departure: dep.date,
+    departureTime: dep.time,
+    arrival: arr.date,
+    arrivalTime: arr.time,
+    airline: meta.airline ?? null,
+    flightNumber: meta.flight_number ?? null,
+    aircraft: meta.aircraft ?? null,
+    aircraftReg: meta.aircraft_reg ?? null,
+    flightReason: meta.flight_reason ?? null,
+    note: reservation.notes ?? null,
+    seats,
+  };
+}
+
+/**
+ * Push a locally-edited linked reservation back to AirTrail using the importer's
+ * (owner's) credentials — even if a different member made the edit. If the owner
+ * is gone or the flight no longer exists in AirTrail, the link is detached so the
+ * next pull's AirTrail-wins policy can't silently revert the local edit.
+ */
+export async function pushReservationToAirtrail(reservationId: number, tripId: number): Promise<void> {
+  if (!syncGloballyEnabled()) return;
+
+  const row = db
+    .prepare(
+      "SELECT id, trip_id, external_id, external_owner_user_id, sync_enabled FROM reservations WHERE id = ? AND external_source = 'airtrail'",
+    )
+    .get(reservationId) as
+    | { id: number; trip_id: number; external_id: string; external_owner_user_id: number | null; sync_enabled: number }
+    | undefined;
+  if (!row || !row.sync_enabled) return;
+
+  const creds: AirtrailCreds | null = row.external_owner_user_id
+    ? getAirtrailCredentials(row.external_owner_user_id)
+    : null;
+  if (!creds) {
+    detach(tripId, row.id); // owner disconnected — cannot push, so stop syncing
+    return;
+  }
+
+  let existing: AirtrailFlightRaw | null;
+  try {
+    existing = await getFlight(creds, Number(row.external_id));
+  } catch (err) {
+    if (err instanceof AirtrailAuthError) detach(tripId, row.id);
+    else logError(`AirTrail push: get failed for reservation ${row.id}: ${err instanceof Error ? err.message : err}`);
+    return;
+  }
+  if (!existing) {
+    detach(tripId, row.id); // gone in AirTrail → treat like a remote delete
+    return;
+  }
+
+  const reservation = getReservationWithJoins(row.id);
+  if (!reservation) return;
+
+  const payload = buildSavePayload(reservation, existing);
+  if (!payload) return;
+
+  try {
+    await saveFlight(creds, payload);
+    // Self-write suppression: re-read the saved flight and store its hash so the
+    // next poll doesn't treat our own write as an inbound change.
+    const saved = await getFlight(creds, Number(row.external_id));
+    if (saved) {
+      db.prepare('UPDATE reservations SET external_hash = ?, external_synced_at = ? WHERE id = ?').run(
+        canonicalHash(saved),
+        new Date().toISOString(),
+        row.id,
+      );
+    }
+  } catch (err) {
+    logError(`AirTrail push failed for reservation ${row.id}: ${err instanceof Error ? err.message : err}`);
+  }
+}

server/src/services/dayService.ts

@@ -157,6 +157,220 @@ export function deleteDay(id: string | number) {
   db.prepare('DELETE FROM days WHERE id = ?').run(id);
 }
 
+// ---------------------------------------------------------------------------
+// Day reorder / insert (#589)
+//
+// Reordering keeps every day ROW stable (so assignments, notes, accommodations,
+// photos and multi-day reservation positions ride along by id) and only changes
+// each row's day_number — its position. On a dated trip the calendar dates stay
+// pinned to their slots (position i keeps the i-th date) and the day's content
+// moves across them. Because a booking's day is derived from the date part of
+// reservation_time, every booking on a day whose date changed gets that date
+// re-stamped onto the day's new date (time-of-day preserved), so day_id stays
+// consistent and the booking moves with its day.
+// ---------------------------------------------------------------------------
+
+const MS_PER_DAY = 24 * 60 * 60 * 1000;
+
+function addDays(date: string, n: number): string {
+  const [y, m, d] = date.split('-').map(Number);
+  const t = Date.UTC(y, m - 1, d) + n * MS_PER_DAY;
+  const dt = new Date(t);
+  const yyyy = dt.getUTCFullYear();
+  const mm = String(dt.getUTCMonth() + 1).padStart(2, '0');
+  const dd = String(dt.getUTCDate()).padStart(2, '0');
+  return `${yyyy}-${mm}-${dd}`;
+}
+
+function dayDelta(from: string, to: string): number {
+  const [fy, fm, fd] = from.split('-').map(Number);
+  const [ty, tm, td] = to.split('-').map(Number);
+  return Math.round((Date.UTC(ty, tm - 1, td) - Date.UTC(fy, fm - 1, fd)) / MS_PER_DAY);
+}
+
+/** Replace the date part of an ISO-ish timestamp, keeping any time suffix. */
+function withDatePart(timestamp: string, date: string): string {
+  return date + (timestamp.length > 10 ? timestamp.slice(10) : '');
+}
+
+/**
+ * After day dates have been re-pinned, re-stamp the date of every booking on a
+ * moved day so reservation_time/reservation_end_time follow their day's new
+ * date (time-of-day preserved). Transport endpoints (flight legs) shift by the
+ * same per-booking day delta so multi-leg timing stays internally consistent.
+ */
+function restampReservationDates(
+  tripId: string | number,
+  oldDateById: Map<number, string | null>,
+  newDateById: Map<number, string | null>,
+): void {
+  const reservations = db.prepare(
+    'SELECT id, day_id, end_day_id, reservation_time, reservation_end_time FROM reservations WHERE trip_id = ?'
+  ).all(tripId) as {
+    id: number; day_id: number | null; end_day_id: number | null;
+    reservation_time: string | null; reservation_end_time: string | null;
+  }[];
+
+  const setTime = db.prepare('UPDATE reservations SET reservation_time = ? WHERE id = ?');
+  const setEndTime = db.prepare('UPDATE reservations SET reservation_end_time = ? WHERE id = ?');
+  const endpoints = db.prepare('SELECT id, local_date FROM reservation_endpoints WHERE reservation_id = ?');
+  const setEndpointDate = db.prepare('UPDATE reservation_endpoints SET local_date = ? WHERE id = ?');
+
+  for (const r of reservations) {
+    if (r.day_id != null && r.reservation_time) {
+      const oldDate = oldDateById.get(r.day_id);
+      const newDate = newDateById.get(r.day_id);
+      if (oldDate && newDate && oldDate !== newDate) {
+        setTime.run(withDatePart(r.reservation_time, newDate), r.id);
+        // Shift each transport leg's local_date by the same number of days.
+        const delta = dayDelta(oldDate, newDate);
+        if (delta !== 0) {
+          for (const ep of endpoints.all(r.id) as { id: number; local_date: string | null }[]) {
+            if (ep.local_date) setEndpointDate.run(addDays(ep.local_date, delta), ep.id);
+          }
+        }
+      }
+    }
+    if (r.end_day_id != null && r.reservation_end_time) {
+      const oldDate = oldDateById.get(r.end_day_id);
+      const newDate = newDateById.get(r.end_day_id);
+      if (oldDate && newDate && oldDate !== newDate) {
+        setEndTime.run(withDatePart(r.reservation_end_time, newDate), r.id);
+      }
+    }
+  }
+}
+
+/** A stay must not end before it begins after a reorder/insert. */
+function assertNoInvertedAccommodation(tripId: string | number): void {
+  const spans = db.prepare(`
+    SELECT a.id, s.day_number AS start_no, e.day_number AS end_no
+    FROM day_accommodations a
+    JOIN days s ON a.start_day_id = s.id
+    JOIN days e ON a.end_day_id = e.id
+    WHERE a.trip_id = ?
+  `).all(tripId) as { id: number; start_no: number; end_no: number }[];
+  for (const span of spans) {
+    if (span.start_no > span.end_no) {
+      throw new DayReorderError('This move would make an accommodation end before it starts.');
+    }
+  }
+}
+
+/** Thrown for invalid reorder/insert requests; mapped to HTTP 400 by the controller. */
+export class DayReorderError extends Error {}
+
+/**
+ * Reorder whole days. `orderedIds` is the desired full sequence of this trip's
+ * day ids (a permutation of the current ids).
+ */
+export function reorderDays(tripId: string | number, orderedIds: number[]) {
+  const rows = db.prepare(
+    'SELECT id, day_number, date FROM days WHERE trip_id = ? ORDER BY day_number'
+  ).all(tripId) as { id: number; day_number: number; date: string | null }[];
+
+  const existingIds = new Set(rows.map(r => r.id));
+  if (orderedIds.length !== rows.length || !orderedIds.every(id => existingIds.has(id))) {
+    throw new DayReorderError('orderedIds must be a permutation of the trip day ids.');
+  }
+
+  const oldDateById = new Map(rows.map(r => [r.id, r.date]));
+  // Dates stay pinned to slots: position i keeps the i-th date (ascending).
+  const sortedDates = rows.map(r => r.date).filter((d): d is string => !!d).sort();
+  const isDated = sortedDates.length > 0;
+
+  const setDayNumber = db.prepare('UPDATE days SET day_number = ? WHERE id = ?');
+  const setDayNumberAndDate = db.prepare('UPDATE days SET day_number = ?, date = ? WHERE id = ?');
+
+  db.exec('BEGIN');
+  try {
+    // Two-phase renumber to dodge UNIQUE(trip_id, day_number) collisions.
+    orderedIds.forEach((id, i) => setDayNumber.run(-(i + 1), id));
+    const newDateById = new Map<number, string | null>();
+    orderedIds.forEach((id, i) => {
+      const date = isDated ? (sortedDates[i] ?? null) : null;
+      setDayNumberAndDate.run(i + 1, date, id);
+      newDateById.set(id, date);
+    });
+
+    if (isDated) restampReservationDates(tripId, oldDateById, newDateById);
+    assertNoInvertedAccommodation(tripId);
+
+    db.exec('COMMIT');
+  } catch (e) {
+    db.exec('ROLLBACK');
+    throw e;
+  }
+
+  return listDays(tripId);
+}
+
+/**
+ * Insert a new empty day at a 1-based position (default: append at the end).
+ * On a dated trip the trip gains one calendar day: dates re-pin so the slots
+ * stay contiguous, the trip's end_date extends by one day, and bookings on
+ * shifted days have their dates re-stamped (same rules as reorderDays).
+ */
+export function insertDay(tripId: string | number, position?: number) {
+  const rows = db.prepare(
+    'SELECT id, day_number, date FROM days WHERE trip_id = ? ORDER BY day_number'
+  ).all(tripId) as { id: number; day_number: number; date: string | null }[];
+  const n = rows.length;
+  const pos = Math.min(Math.max(position ?? n + 1, 1), n + 1);
+  const datedRows = rows.filter(r => r.date) as { id: number; day_number: number; date: string }[];
+  const isDated = datedRows.length > 0;
+
+  const setDayNumber = db.prepare('UPDATE days SET day_number = ? WHERE id = ?');
+
+  if (!isDated) {
+    db.exec('BEGIN');
+    try {
+      const toShift = rows.filter(r => r.day_number >= pos);
+      toShift.forEach(r => setDayNumber.run(-r.day_number, r.id));
+      const result = db.prepare('INSERT INTO days (trip_id, day_number, date) VALUES (?, ?, NULL)').run(tripId, pos);
+      toShift.forEach(r => setDayNumber.run(r.day_number + 1, r.id));
+      db.exec('COMMIT');
+      const day = db.prepare('SELECT * FROM days WHERE id = ?').get(result.lastInsertRowid) as Day;
+      return { ...day, assignments: [], notes_items: [] };
+    } catch (e) {
+      db.exec('ROLLBACK');
+      throw e;
+    }
+  }
+
+  // Dated trip: rebuild N+1 contiguous dates from the earliest date.
+  const start = datedRows.map(r => r.date).sort()[0];
+  const dates = Array.from({ length: n + 1 }, (_, i) => addDays(start, i));
+  const oldDateById = new Map(rows.map(r => [r.id, r.date]));
+  const setDayNumberAndDate = db.prepare('UPDATE days SET day_number = ?, date = ? WHERE id = ?');
+
+  db.exec('BEGIN');
+  try {
+    rows.forEach((r, i) => setDayNumber.run(-(i + 1), r.id));
+    const result = db.prepare('INSERT INTO days (trip_id, day_number, date) VALUES (?, ?, ?)').run(tripId, pos, dates[pos - 1]);
+    const newId = Number(result.lastInsertRowid);
+
+    const orderedIds = rows.map(r => r.id);
+    orderedIds.splice(pos - 1, 0, newId);
+    const newDateById = new Map<number, string | null>();
+    orderedIds.forEach((id, i) => {
+      setDayNumberAndDate.run(i + 1, dates[i], id);
+      newDateById.set(id, dates[i]);
+    });
+
+    restampReservationDates(tripId, oldDateById, newDateById);
+    assertNoInvertedAccommodation(tripId);
+    db.prepare('UPDATE trips SET end_date = ? WHERE id = ?').run(dates[dates.length - 1], tripId);
+
+    db.exec('COMMIT');
+    const day = db.prepare('SELECT * FROM days WHERE id = ?').get(newId) as Day;
+    return { ...day, assignments: [], notes_items: [] };
+  } catch (e) {
+    db.exec('ROLLBACK');
+    throw e;
+  }
+}
+
 // ---------------------------------------------------------------------------
 // Accommodation helpers
 // ---------------------------------------------------------------------------

server/src/services/inAppNotifications.ts

@@ -3,6 +3,13 @@ import { broadcastToUser } from '../websocket';
 import { getAction } from './inAppNotificationActions';
 import { isEnabledForEvent, type NotifEventType } from './notificationPreferencesService';
 
+// SQLite's CURRENT_TIMESTAMP is UTC but the string ('YYYY-MM-DD HH:MM:SS') has
+// no 'T'/'Z', so `new Date(...)` parses it as LOCAL time. Normalize to ISO-UTC
+// so the client renders notification times in the viewer's own timezone (#1149).
+function toUtcIso(ts: string): string {
+  return ts.endsWith('Z') ? ts : ts.replace(' ', 'T') + 'Z';
+}
+
 type NotificationType = 'simple' | 'boolean' | 'navigate';
 type NotificationScope = 'trip' | 'user' | 'admin';
 type NotificationResponse = 'positive' | 'negative';
@@ -218,6 +225,7 @@ export function createNotificationForRecipient(
     type: 'notification:new',
     notification: {
       ...row,
+      created_at: toUtcIso(row.created_at),
       sender_username: sender?.username ?? null,
       sender_avatar: sender?.avatar ? `/uploads/avatars/${sender.avatar}` : null,
     },
@@ -251,6 +259,7 @@ function getNotifications(
 
   const mapped = rows.map(r => ({
     ...r,
+    created_at: toUtcIso(r.created_at),
     sender_avatar: r.sender_avatar ? `/uploads/avatars/${r.sender_avatar}` : null,
   }));
 

server/src/services/mapsService.ts

@@ -204,6 +204,210 @@ export async function fetchOverpassDetails(osmType: string, osmId: string): Prom
   } catch { return null; }
 }
 
+// ── Overpass POI search (by category within a viewport bbox) ─────────────────
+// Powers the "explore places on the map" pill. OSM-ONLY by design — this never
+// calls Google, even when a Google key is configured.
+
+export interface OverpassPoi {
+  osm_id: string; // 'node:123' | 'way:123' | 'relation:123' (matches the placeId format elsewhere)
+  name: string;
+  lat: number;
+  lng: number;
+  category: string; // the requested pill category key, e.g. 'restaurant'
+  poi_type: string; // the raw OSM tag that matched, e.g. 'amenity=restaurant'
+  address: string | null;
+  website: string | null;
+  phone: string | null;
+  opening_hours: string | null;
+  cuisine: string | null;
+  source: 'openstreetmap';
+}
+
+// Each pill category → the OSM tag selectors it searches. Keys here are the
+// contract with the client's POI_CATEGORIES (same keys, label/icon/colour live
+// client-side).
+const CATEGORY_OSM_FILTERS: Record<string, string[]> = {
+  restaurant: ['amenity=restaurant', 'amenity=fast_food'],
+  cafe: ['amenity=cafe'],
+  bar: ['amenity=bar', 'amenity=pub', 'amenity=nightclub'],
+  hotel: ['tourism=hotel', 'tourism=hostel', 'tourism=guest_house', 'tourism=apartment', 'tourism=motel'],
+  sights: ['tourism=attraction', 'tourism=viewpoint', 'historic=monument', 'historic=castle', 'historic=memorial', 'historic=ruins'],
+  museum: ['tourism=museum', 'tourism=gallery', 'tourism=artwork', 'amenity=theatre'],
+  nature: ['leisure=park', 'leisure=garden', 'natural=beach', 'natural=peak'],
+  activity: ['tourism=theme_park', 'tourism=zoo', 'tourism=aquarium', 'leisure=water_park'],
+  shopping: ['shop=mall', 'shop=department_store', 'amenity=marketplace'],
+  supermarket: ['shop=supermarket', 'shop=convenience'],
+};
+
+export const POI_CATEGORY_KEYS = Object.keys(CATEGORY_OSM_FILTERS);
+
+interface OverpassPoiElement {
+  type: string;
+  id: number;
+  lat?: number;
+  lon?: number;
+  center?: { lat: number; lon: number };
+  tags?: Record<string, string>;
+}
+
+interface PoiSearchResult {
+  pois: OverpassPoi[];
+  source: 'openstreetmap';
+  truncated: boolean;
+  // True when the requested viewport was too large and got shrunk to a centred
+  // window before querying — the results then cover the middle of the view only.
+  clamped: boolean;
+}
+
+// Public Overpass mirrors, queried in PARALLEL (first valid response wins).
+// Reachability and load vary a lot by network/region — the canonical instance is
+// frequently overloaded (504s) and some community mirrors are unreachable from
+// certain networks. Racing them means whichever mirror is fastest-reachable for
+// this user answers, and an overloaded or blocked one never blocks the others.
+const OVERPASS_MIRRORS = [
+  'https://overpass-api.de/api/interpreter',
+  'https://maps.mail.ru/osm/tools/overpass/api/interpreter',
+  'https://overpass.kumi.systems/api/interpreter',
+  'https://overpass.private.coffee/api/interpreter',
+];
+// Per-mirror cap. Because mirrors race in parallel this is also the worst-case
+// total wait before every mirror is given up on and a 502 is returned.
+const OVERPASS_TIMEOUT_MS = 12000;
+// Largest viewport side we send to Overpass. A country/continent-sized bbox makes
+// Overpass scan millions of elements and time out; clamping to a centred window
+// keeps the query cheap so the explore pill returns fast at ANY zoom level.
+const MAX_BBOX_SPAN_DEG = 0.5;
+
+// Short-lived cache so panning back over / re-toggling the same area doesn't
+// re-hit Overpass. Keyed by category + rounded (post-clamp) bbox.
+const POI_CACHE = new Map<string, { at: number; value: PoiSearchResult }>();
+const POI_CACHE_TTL_MS = 5 * 60 * 1000;
+// Cap the number of cached areas so panning across the globe can't grow the map
+// without bound (entries are evicted oldest-first once the cap is reached).
+const POI_CACHE_MAX = 500;
+
+// POST the query to all mirrors at once and return the first one that answers with
+// valid JSON. Throws {status:502} only if every mirror fails. Racing (rather than
+// trying one-by-one) keeps latency at the fastest reachable mirror instead of the
+// sum of every dead mirror's timeout.
+async function overpassFetch(query: string): Promise<OverpassPoiElement[]> {
+  const body = `data=${encodeURIComponent(query)}`;
+  const controllers: AbortController[] = [];
+
+  const attempt = async (url: string): Promise<OverpassPoiElement[]> => {
+    const ctrl = new AbortController();
+    controllers.push(ctrl);
+    const timer = setTimeout(() => ctrl.abort(), OVERPASS_TIMEOUT_MS);
+    try {
+      const res = await fetch(url, {
+        method: 'POST',
+        headers: { 'User-Agent': UA, 'Content-Type': 'application/x-www-form-urlencoded' },
+        body,
+        signal: ctrl.signal,
+      });
+      if (!res.ok) throw new Error(`Overpass ${res.status} @ ${url}`);
+      const data = await res.json() as { elements?: OverpassPoiElement[]; remark?: string };
+      // Overpass signals an internal timeout / runtime error via `remark` while
+      // still answering HTTP 200 — often fast, with an empty or partial element
+      // set. Treat that as a failed attempt so a healthy mirror wins the race
+      // instead of this fast-but-empty answer, and so the all-mirrors-failed path
+      // still surfaces a real error to the client instead of a silent "no places".
+      if (data.remark) throw new Error(`Overpass remark @ ${url}: ${data.remark}`);
+      if (!Array.isArray(data.elements)) throw new Error(`Overpass non-OSM body @ ${url}`);
+      return data.elements;
+    } finally {
+      clearTimeout(timer);
+    }
+  };
+
+  try {
+    // Promise.any resolves with the first mirror to return valid JSON, and only
+    // rejects (AggregateError) once every mirror has failed.
+    return await Promise.any(OVERPASS_MIRRORS.map(attempt));
+  } catch {
+    throw Object.assign(new Error('Overpass request failed'), { status: 502 });
+  } finally {
+    // Cancel the slower/losing requests — we already have (or have given up on) a result.
+    controllers.forEach(c => { try { c.abort(); } catch { /* noop */ } });
+  }
+}
+
+export async function searchOverpassPois(
+  category: string,
+  bbox: { south: number; west: number; north: number; east: number },
+  limit = 60,
+): Promise<PoiSearchResult> {
+  const filters = CATEGORY_OSM_FILTERS[category];
+  if (!filters) throw Object.assign(new Error('Unknown POI category'), { status: 400 });
+
+  // Clamp an oversized viewport to a centred window so the query stays cheap and
+  // returns fast at any zoom, instead of timing out / 502-ing on a huge area.
+  let { south, west, north, east } = bbox;
+  let clamped = false;
+  if (north - south > MAX_BBOX_SPAN_DEG) {
+    const c = (north + south) / 2;
+    south = c - MAX_BBOX_SPAN_DEG / 2;
+    north = c + MAX_BBOX_SPAN_DEG / 2;
+    clamped = true;
+  }
+  if (east - west > MAX_BBOX_SPAN_DEG) {
+    const c = (east + west) / 2;
+    west = c - MAX_BBOX_SPAN_DEG / 2;
+    east = c + MAX_BBOX_SPAN_DEG / 2;
+    clamped = true;
+  }
+
+  // Serve repeat pans/toggles of the same area straight from the cache.
+  const cacheKey = `${category}|${south.toFixed(2)},${west.toFixed(2)},${north.toFixed(2)},${east.toFixed(2)}|${limit}`;
+  const cached = POI_CACHE.get(cacheKey);
+  if (cached && Date.now() - cached.at < POI_CACHE_TTL_MS) return cached.value;
+  if (cached) POI_CACHE.delete(cacheKey); // expired — drop it before refetching
+
+  // Overpass wants the box as (south,west,north,east) = (minLat,minLng,maxLat,maxLng).
+  const box = `(${south},${west},${north},${east})`;
+  const selectors = filters.map(f => {
+    const [k, v] = f.split('=');
+    return `  nwr["${k}"="${v}"]${box};`;
+  }).join('\n');
+  // `out center tags <n>` returns ways/relations with a computed center and caps
+  // the result count in one round-trip.
+  const query = `[out:json][timeout:20];\n(\n${selectors}\n);\nout center tags ${limit + 25};`;
+
+  const elements = await overpassFetch(query);
+
+  const pois: OverpassPoi[] = [];
+  for (const el of elements) {
+    const tags = el.tags || {};
+    const name = tags.name || tags['name:en'] || tags.brand || null;
+    if (!name) continue; // unnamed POIs aren't useful to add to a plan
+    const lat = el.lat ?? el.center?.lat;
+    const lng = el.lon ?? el.center?.lon;
+    if (lat == null || lng == null) continue;
+    const matched = filters.find(f => { const [k, v] = f.split('='); return tags[k] === v; }) || filters[0];
+    const addr = [tags['addr:street'], tags['addr:housenumber'], tags['addr:postcode'], tags['addr:city']].filter(Boolean).join(' ') || null;
+    pois.push({
+      osm_id: `${el.type}:${el.id}`,
+      name,
+      lat,
+      lng,
+      category,
+      poi_type: matched,
+      address: addr,
+      website: tags.website || tags['contact:website'] || null,
+      phone: tags.phone || tags['contact:phone'] || null,
+      opening_hours: tags.opening_hours || null,
+      cuisine: tags.cuisine || null,
+      source: 'openstreetmap',
+    });
+  }
+  const truncated = pois.length > limit;
+  const value: PoiSearchResult = { pois: pois.slice(0, limit), source: 'openstreetmap', truncated, clamped };
+  // FIFO eviction: a Map preserves insertion order, so the first key is the oldest.
+  if (POI_CACHE.size >= POI_CACHE_MAX) POI_CACHE.delete(POI_CACHE.keys().next().value as string);
+  POI_CACHE.set(cacheKey, { at: Date.now(), value });
+  return value;
+}
+
 // ── Opening hours parsing ────────────────────────────────────────────────────
 
 export function parseOpeningHours(ohString: string): { weekdayDescriptions: string[]; openNow: boolean | null } {
@@ -342,7 +546,7 @@ export async function fetchWikimediaPhoto(lat: number, lng: number, name?: strin
 
 // ── Search places (Google or Nominatim fallback) ─────────────────────────────
 
-export async function searchPlaces(userId: number, query: string, lang?: string): Promise<{ places: Record<string, unknown>[]; source: string }> {
+export async function searchPlaces(userId: number, query: string, lang?: string, locationBias?: { lat: number; lng: number; radius?: number }): Promise<{ places: Record<string, unknown>[]; source: string }> {
   const apiKey = getMapsKey(userId);
 
   if (!apiKey) {
@@ -350,6 +554,18 @@ export async function searchPlaces(userId: number, query: string, lang?: string)
     return { places, source: 'openstreetmap' };
   }
 
+  const searchBody: Record<string, unknown> = { textQuery: query, languageCode: toApiLang(lang) };
+  // Bias results toward the caller's area when supplied — without it Google Text
+  // Search falls back to the API key's billing region, which skews foreign-region queries.
+  if (locationBias) {
+    searchBody.locationBias = {
+      circle: {
+        center: { latitude: locationBias.lat, longitude: locationBias.lng },
+        radius: locationBias.radius ?? 50000,
+      },
+    };
+  }
+
   const response = await googleFetch('https://places.googleapis.com/v1/places:searchText', 'searchText', {
     method: 'POST',
     headers: {
@@ -357,7 +573,7 @@ export async function searchPlaces(userId: number, query: string, lang?: string)
       'X-Goog-Api-Key': apiKey,
       'X-Goog-FieldMask': 'places.id,places.displayName,places.formattedAddress,places.location,places.rating,places.websiteUri,places.nationalPhoneNumber,places.types',
     },
-    body: JSON.stringify({ textQuery: query, languageCode: toApiLang(lang) }),
+    body: JSON.stringify(searchBody),
   });
 
   const data = await response.json() as { places?: GooglePlaceResult[]; error?: { message?: string } };
@@ -377,6 +593,7 @@ export async function searchPlaces(userId: number, query: string, lang?: string)
     rating: p.rating || null,
     website: p.websiteUri || null,
     phone: p.nationalPhoneNumber || null,
+    types: p.types || [],
     source: 'google',
   }));
 

server/src/services/packingService.ts

@@ -1,7 +1,7 @@
 import { db } from '../db/database';
 import { avatarUrl } from './authService';
 
-const BAG_COLORS = ['#6366f1', '#ec4899', '#f97316', '#10b981', '#06b6d4', '#8b5cf6', '#ef4444', '#f59e0b'];
+const BAG_COLORS = ['#6366f1', '#ec4899', '#f97316', '#10b981', '#06b6d4', '#8b5cf6', '#ef4444', '#f59e0b', '#3b82f6', '#84cc16', '#d946ef', '#14b8a6', '#f43f5e', '#a855f7', '#eab308', '#64748b'];
 
 export { verifyTripAccess } from './tripAccess';
 
@@ -76,13 +76,14 @@ interface ImportItem {
   category?: string;
   weight_grams?: string | number;
   bag?: string;
+  quantity?: number;
 }
 
 export function bulkImport(tripId: string | number, items: ImportItem[]) {
   const maxOrder = db.prepare('SELECT MAX(sort_order) as max FROM packing_items WHERE trip_id = ?').get(tripId) as { max: number | null };
   let sortOrder = (maxOrder.max !== null ? maxOrder.max : -1) + 1;
 
-  const stmt = db.prepare('INSERT INTO packing_items (trip_id, name, checked, category, weight_grams, bag_id, sort_order) VALUES (?, ?, ?, ?, ?, ?, ?)');
+  const stmt = db.prepare('INSERT INTO packing_items (trip_id, name, checked, category, weight_grams, bag_id, sort_order, quantity) VALUES (?, ?, ?, ?, ?, ?, ?, ?)');
   const created: any[] = [];
 
   const insertAll = db.transaction(() => {
@@ -105,7 +106,8 @@ export function bulkImport(tripId: string | number, items: ImportItem[]) {
         }
       }
 
-      const result = stmt.run(tripId, item.name.trim(), checked, item.category?.trim() || 'Other', weight, bagId, sortOrder++);
+      const qty = Math.max(1, Math.min(999, Number(item.quantity) || 1));
+      const result = stmt.run(tripId, item.name.trim(), checked, item.category?.trim() || 'Other', weight, bagId, sortOrder++, qty);
       created.push(db.prepare('SELECT * FROM packing_items WHERE id = ?').get(result.lastInsertRowid));
     }
   });

server/src/services/placeEnrichment.ts

@@ -0,0 +1,164 @@
+import { db, getPlaceWithTags } from '../db/database';
+import { broadcast } from '../websocket';
+import { getMapsKey, searchPlaces, getPlacePhoto } from './mapsService';
+
+/**
+ * Background enrichment for list-imported places (#886).
+ *
+ * Google/Naver list imports only carry name + coordinates, so the imported
+ * places open as bare pins (the Maps tab jumps to coordinates, no photo, no
+ * open/closed). When the importer opts in and a Google Maps key is configured,
+ * we re-resolve each place by name — biased to and validated against the
+ * imported coordinates — to a real Google place, then fill in the empty fields
+ * and persist the resolved `google_place_id` (which is what powers on-demand
+ * opening hours / the proper Maps link going forward).
+ *
+ * This runs detached from the import request (fire-and-forget) so a long list
+ * never blocks the response, and pushes each enriched row over the websocket so
+ * the sidebar fills in progressively. It only ever fills EMPTY columns, so it
+ * can never clobber data the import already captured (e.g. a Naver address).
+ */
+
+/** A place the import produced — only the fields enrichment reads/writes. */
+export interface EnrichablePlace {
+  id: number;
+  name: string;
+  lat: number;
+  lng: number;
+  google_place_id?: string | null;
+  address?: string | null;
+  website?: string | null;
+  phone?: string | null;
+  image_url?: string | null;
+}
+
+/** How close a search hit must be to the imported coordinates to be trusted. */
+const MATCH_RADIUS_METERS = 250;
+/** Bias the text search to roughly the imported area. */
+const SEARCH_BIAS_RADIUS_METERS = 2000;
+/** Concurrent enrichment lookups — small, to stay friendly to the Maps quota. */
+const ENRICH_CONCURRENCY = 3;
+
+function haversineMeters(a: { lat: number; lng: number }, b: { lat: number; lng: number }): number {
+  const R = 6371000;
+  const toRad = (d: number) => (d * Math.PI) / 180;
+  const dLat = toRad(b.lat - a.lat);
+  const dLng = toRad(b.lng - a.lng);
+  const lat1 = toRad(a.lat);
+  const lat2 = toRad(b.lat);
+  const h = Math.sin(dLat / 2) ** 2 + Math.cos(lat1) * Math.cos(lat2) * Math.sin(dLng / 2) ** 2;
+  return 2 * R * Math.asin(Math.sqrt(h));
+}
+
+/**
+ * Pick the search result that is the same place as the import: it must be a
+ * Google result (have a google_place_id) with coordinates within
+ * MATCH_RADIUS_METERS of the imported point. Returns the closest such hit, or
+ * null when nothing is close enough — in which case the place is left as
+ * imported rather than risking a wrong-place overwrite (common-name / romanized
+ * lists). Exported for unit testing.
+ */
+export function pickEnrichmentMatch(
+  candidates: Record<string, unknown>[],
+  target: { lat: number; lng: number },
+  maxMeters: number = MATCH_RADIUS_METERS,
+): Record<string, unknown> | null {
+  let best: { c: Record<string, unknown>; dist: number } | null = null;
+  for (const c of candidates || []) {
+    const gpid = c.google_place_id;
+    const lat = c.lat;
+    const lng = c.lng;
+    if (typeof gpid !== 'string' || !gpid) continue;
+    if (typeof lat !== 'number' || typeof lng !== 'number') continue;
+    const dist = haversineMeters(target, { lat, lng });
+    if (dist > maxMeters) continue;
+    if (!best || dist < best.dist) best = { c, dist };
+  }
+  return best?.c ?? null;
+}
+
+async function mapWithConcurrency<T>(items: T[], limit: number, fn: (item: T) => Promise<void>): Promise<void> {
+  let cursor = 0;
+  const workers = Array.from({ length: Math.min(limit, items.length) }, async () => {
+    while (cursor < items.length) {
+      const item = items[cursor++];
+      await fn(item);
+    }
+  });
+  await Promise.all(workers);
+}
+
+const str = (v: unknown): string | null => (typeof v === 'string' && v.trim() ? v.trim() : null);
+
+async function enrichOne(tripId: string, userId: number, place: EnrichablePlace, lang?: string): Promise<void> {
+  // Already linked (shouldn't happen for list imports) — nothing to resolve.
+  if (place.google_place_id) return;
+  if (typeof place.lat !== 'number' || typeof place.lng !== 'number') return;
+
+  const { places: results } = await searchPlaces(userId, place.name, lang, {
+    lat: place.lat,
+    lng: place.lng,
+    radius: SEARCH_BIAS_RADIUS_METERS,
+  });
+  const match = pickEnrichmentMatch(results, { lat: place.lat, lng: place.lng });
+  if (!match) return;
+
+  const gpid = str(match.google_place_id);
+  if (!gpid) return;
+
+  // COALESCE so enrichment only fills empty columns — never overwrites data the
+  // import already captured (e.g. Naver's address) or anything the user edited.
+  db.prepare(
+    `UPDATE places
+       SET google_place_id = COALESCE(google_place_id, ?),
+           address         = COALESCE(address, ?),
+           website         = COALESCE(website, ?),
+           phone           = COALESCE(phone, ?),
+           updated_at      = CURRENT_TIMESTAMP
+     WHERE id = ? AND trip_id = ?`,
+  ).run(gpid, str(match.address), str(match.website), str(match.phone), place.id, tripId);
+
+  // Photo is best-effort: Google often has none, and getPlacePhoto throws 404 in
+  // that case — a missing photo must never abort the rest of the enrichment.
+  try {
+    const photo = await getPlacePhoto(userId, gpid, place.lat, place.lng, place.name);
+    if (photo?.photoUrl) {
+      db.prepare(
+        'UPDATE places SET image_url = COALESCE(image_url, ?), updated_at = CURRENT_TIMESTAMP WHERE id = ? AND trip_id = ?',
+      ).run(photo.photoUrl, place.id, tripId);
+    }
+  } catch {
+    /* no photo — leave image_url as-is */
+  }
+
+  // Push the enriched row to every connected client (no socket exclusion: the
+  // importer's own client should also receive the late update).
+  const updated = getPlaceWithTags(place.id);
+  if (updated) broadcast(tripId, 'place:updated', { place: updated }, undefined);
+}
+
+/**
+ * Enrich a batch of just-imported places in the background. Never throws —
+ * any per-place failure is swallowed so one bad lookup can't take down the
+ * detached task or the process. No-ops when no Google Maps key is configured.
+ */
+export async function enrichImportedPlaces(
+  tripId: string,
+  userId: number,
+  places: EnrichablePlace[],
+  lang?: string,
+): Promise<void> {
+  try {
+    if (!places.length) return;
+    if (!getMapsKey(userId)) return;
+    await mapWithConcurrency(places, ENRICH_CONCURRENCY, async (place) => {
+      try {
+        await enrichOne(tripId, userId, place, lang);
+      } catch (err) {
+        console.error(`[Places] enrichment failed for place ${place.id}:`, err instanceof Error ? err.message : err);
+      }
+    });
+  } catch (err) {
+    console.error('[Places] import enrichment pass failed:', err instanceof Error ? err.message : err);
+  }
+}

server/src/services/placeService.ts

@@ -13,6 +13,14 @@ import {
   resolveCategoryIdForFolder,
   type KmlImportSummary,
 } from './kmlImport';
+import { enrichImportedPlaces, type EnrichablePlace } from './placeEnrichment';
+
+/** Opt-in Places-API enrichment for list imports (#886). */
+export interface ListImportOptions {
+  enrich?: boolean;
+  userId?: number;
+  lang?: string;
+}
 
 interface PlaceWithCategory extends Place {
   category_name: string | null;
@@ -595,7 +603,7 @@ export async function importMapFile(tripId: string, fileBuffer: Buffer, filename
 // Import Google Maps list
 // ---------------------------------------------------------------------------
 
-export async function importGoogleList(tripId: string, url: string) {
+export async function importGoogleList(tripId: string, url: string, opts?: ListImportOptions) {
   let listId: string | null = null;
   let resolvedUrl = url;
 
@@ -697,6 +705,10 @@ export async function importGoogleList(tripId: string, url: string) {
   });
   insertAll();
 
+  if (opts?.enrich && opts.userId && created.length) {
+    void enrichImportedPlaces(tripId, opts.userId, created as EnrichablePlace[], opts.lang);
+  }
+
   return { places: created, listName, skipped };
 }
 
@@ -707,6 +719,7 @@ export async function importGoogleList(tripId: string, url: string) {
 export async function importNaverList(
   tripId: string,
   url: string,
+  opts?: ListImportOptions,
 ): Promise<{ places: any[]; listName: string; skipped: number } | { error: string; status: number }> {
   let resolvedUrl = url;
   const limit = 20;
@@ -826,6 +839,10 @@ export async function importNaverList(
   });
   insertAll();
 
+  if (opts?.enrich && opts.userId && created.length) {
+    void enrichImportedPlaces(tripId, opts.userId, created as EnrichablePlace[], opts.lang);
+  }
+
   return { places: created, listName, skipped };
 }
 

server/src/services/settingsService.ts

@@ -12,6 +12,13 @@ export const DEFAULTABLE_USER_SETTING_KEYS = [
   'time_format',
   'blur_booking_codes',
   'map_tile_url',
+  // Instance-wide Mapbox defaults: an admin can set a shared token + style so the
+  // whole instance uses Mapbox without each user pasting their own key (#920).
+  'map_provider',
+  'mapbox_access_token',
+  'mapbox_style',
+  'mapbox_3d_enabled',
+  'mapbox_quality_mode',
 ] as const;
 
 type DefaultableKey = typeof DEFAULTABLE_USER_SETTING_KEYS[number];
@@ -20,9 +27,10 @@ const VALID_VALUES: Partial<Record<DefaultableKey, unknown[]>> = {
   temperature_unit: ['fahrenheit', 'celsius'],
   time_format: ['12h', '24h'],
   dark_mode: [true, false, 'light', 'dark', 'auto'],
+  map_provider: ['leaflet', 'mapbox-gl'],
 };
 
-const BOOLEAN_KEYS = new Set<DefaultableKey>(['blur_booking_codes']);
+const BOOLEAN_KEYS = new Set<DefaultableKey>(['blur_booking_codes', 'mapbox_3d_enabled', 'mapbox_quality_mode']);
 
 function parseValue(raw: string): unknown {
   try { return JSON.parse(raw); } catch { return raw; }
@@ -35,7 +43,11 @@ export function getAdminUserDefaults(): Record<string, unknown> {
   const defaults: Record<string, unknown> = {};
   for (const row of rows) {
     const settingKey = row.key.slice('default_user_setting_'.length);
-    defaults[settingKey] = parseValue(row.value);
+    if (ENCRYPTED_SETTING_KEYS.has(settingKey)) {
+      defaults[settingKey] = row.value ? (decrypt_api_key(row.value) ?? '') : '';
+    } else {
+      defaults[settingKey] = parseValue(row.value);
+    }
   }
   return defaults;
 }
@@ -70,7 +82,12 @@ export function setAdminUserDefaults(partial: Record<string, unknown>): void {
         throw new Error(`Invalid value for ${key}: ${value}`);
       }
 
-      upsert.run(appKey, JSON.stringify(value));
+      // Encrypt sensitive defaults (the shared Mapbox token) at rest, like the
+      // per-user equivalents; everything else is stored as plain JSON.
+      const stored = ENCRYPTED_SETTING_KEYS.has(key)
+        ? (maybe_encrypt_api_key(String(value)) ?? String(value))
+        : JSON.stringify(value);
+      upsert.run(appKey, stored);
     }
     db.exec('COMMIT');
   } catch (err) {

server/src/services/tripService.ts

@@ -543,8 +543,14 @@ export function exportICS(tripId: string | number): { ics: string; filename: str
     if (r.confirmation_number) desc += `\nConfirmation: ${r.confirmation_number}`;
     if (meta.airline) desc += `\nAirline: ${meta.airline}`;
     if (meta.flight_number) desc += `\nFlight: ${meta.flight_number}`;
-    if (meta.departure_airport) desc += `\nFrom: ${meta.departure_airport}`;
-    if (meta.arrival_airport) desc += `\nTo: ${meta.arrival_airport}`;
+    if (Array.isArray(meta.legs) && meta.legs.length > 1) {
+      // Multi-leg flight: show the whole route (FRA → BER → HND) on one event.
+      const stops = [meta.legs[0]?.from, ...meta.legs.map((l: { to?: string }) => l.to)].filter(Boolean);
+      if (stops.length) desc += `\nRoute: ${stops.join(' → ')}`;
+    } else {
+      if (meta.departure_airport) desc += `\nFrom: ${meta.departure_airport}`;
+      if (meta.arrival_airport) desc += `\nTo: ${meta.arrival_airport}`;
+    }
     if (meta.train_number) desc += `\nTrain: ${meta.train_number}`;
     if (r.notes) desc += `\n${r.notes}`;
     if (desc) ics += `DESCRIPTION:${esc(desc)}\r\n`;

server/tests/integration/dayReorder.test.ts

@@ -0,0 +1,134 @@
+/**
+ * Day reorder + insert integration tests (#589) — exercises the real
+ * dayService against the real schema. Covers: position renumber, dates pinned
+ * to slots while content rides along by id, booking-date re-stamp, permutation
+ * validation, the accommodation-inversion guard, and insert (dated + dateless).
+ */
+import { describe, it, expect, vi, beforeAll, beforeEach, afterAll } from 'vitest';
+
+const { testDb, dbMock } = vi.hoisted(() => {
+  // eslint-disable-next-line @typescript-eslint/no-require-imports
+  const Database = require('better-sqlite3');
+  const db = new Database(':memory:');
+  db.exec('PRAGMA journal_mode = WAL');
+  db.exec('PRAGMA foreign_keys = ON');
+  db.exec('PRAGMA busy_timeout = 5000');
+  return { testDb: db, dbMock: { db, closeDb: () => {}, reinitialize: () => {}, canAccessTrip: vi.fn() } };
+});
+
+vi.mock('../../src/db/database', () => dbMock);
+vi.mock('../../src/config', () => ({
+  JWT_SECRET: 'test-jwt-secret-for-trek-testing-only',
+  ENCRYPTION_KEY: 'a1b2c3d4e5f6a7b8c9d0e1f2a3b4c5d6a7b8c9d0e1f2a3b4c5d6a7b8c9d0e1f2',
+  updateJwtSecret: () => {},
+  DEFAULT_LANGUAGE: 'en',
+}));
+
+import { createTables } from '../../src/db/schema';
+import { runMigrations } from '../../src/db/migrations';
+import { resetTestDb } from '../helpers/test-db';
+import { createUser, createTrip, createPlace, createDay, createDayAssignment, createReservation, createDayAccommodation } from '../helpers/factories';
+import { reorderDays, insertDay, DayReorderError } from '../../src/services/dayService';
+
+let userId: number;
+
+beforeAll(() => {
+  createTables(testDb);
+  runMigrations(testDb);
+});
+
+beforeEach(() => {
+  resetTestDb(testDb);
+  userId = createUser(testDb).user.id;
+});
+
+afterAll(() => testDb.close());
+
+const orderedDays = (tripId: number) =>
+  testDb.prepare('SELECT id, day_number, date FROM days WHERE trip_id = ? ORDER BY day_number').all(tripId) as
+    { id: number; day_number: number; date: string | null }[];
+
+describe('reorderDays', () => {
+  it('permutes positions, pins dates to slots, and content rides along by id', () => {
+    const trip = createTrip(testDb, userId, { start_date: '2026-03-01', end_date: '2026-03-03' });
+    const [d1, d2, d3] = orderedDays(trip.id);
+    const place = createPlace(testDb, trip.id);
+    createDayAssignment(testDb, d2.id, place.id); // place sits on day 2
+
+    // Move day 2 to the front: [d2, d1, d3]
+    reorderDays(trip.id, [d2.id, d1.id, d3.id]);
+
+    const after = orderedDays(trip.id);
+    expect(after.map(d => d.id)).toEqual([d2.id, d1.id, d3.id]);
+    // Dates stay pinned to their calendar slots
+    expect(after.map(d => d.date)).toEqual(['2026-03-01', '2026-03-02', '2026-03-03']);
+    // The place rides along with its day row (still attached to d2.id, now at slot 1)
+    const onD2 = testDb.prepare('SELECT * FROM day_assignments WHERE day_id = ?').all(d2.id);
+    expect(onD2).toHaveLength(1);
+  });
+
+  it('re-stamps a booking\'s date onto its day\'s new date, keeping the time', () => {
+    const trip = createTrip(testDb, userId, { start_date: '2026-03-01', end_date: '2026-03-03' });
+    const [d1, d2, d3] = orderedDays(trip.id);
+    const res = createReservation(testDb, trip.id, { day_id: d2.id, type: 'restaurant' });
+    testDb.prepare('UPDATE reservations SET reservation_time = ? WHERE id = ?').run('2026-03-02T19:00', res.id);
+
+    reorderDays(trip.id, [d2.id, d1.id, d3.id]); // d2 moves to the 2026-03-01 slot
+
+    const r = testDb.prepare('SELECT reservation_time FROM reservations WHERE id = ?').get(res.id) as { reservation_time: string };
+    expect(r.reservation_time).toBe('2026-03-01T19:00');
+  });
+
+  it('rejects an orderedIds list that is not a permutation of the trip days', () => {
+    const trip = createTrip(testDb, userId, { start_date: '2026-03-01', end_date: '2026-03-03' });
+    const [d1, d2] = orderedDays(trip.id);
+    expect(() => reorderDays(trip.id, [d1.id, d2.id])).toThrow(DayReorderError);
+  });
+
+  it('blocks a move that would make an accommodation end before it starts, and rolls back', () => {
+    const trip = createTrip(testDb, userId, { start_date: '2026-03-01', end_date: '2026-03-03' });
+    const [d1, d2, d3] = orderedDays(trip.id);
+    const place = createPlace(testDb, trip.id);
+    createDayAccommodation(testDb, trip.id, place.id, d1.id, d2.id); // stay spans day 1 -> day 2
+
+    // Put the start day (d1) after the end day (d2): [d2, d3, d1]
+    expect(() => reorderDays(trip.id, [d2.id, d3.id, d1.id])).toThrow(DayReorderError);
+
+    // Transaction rolled back: original order intact
+    expect(orderedDays(trip.id).map(d => d.id)).toEqual([d1.id, d2.id, d3.id]);
+  });
+});
+
+describe('insertDay', () => {
+  it('inserts an empty day at a position on a dateless trip and shifts the rest', () => {
+    const trip = createTrip(testDb, userId);
+    const d1 = createDay(testDb, trip.id);
+    const d2 = createDay(testDb, trip.id);
+    const d3 = createDay(testDb, trip.id);
+
+    const created = insertDay(trip.id, 1);
+
+    const after = orderedDays(trip.id);
+    expect(after).toHaveLength(4);
+    expect(after[0].id).toBe(created.id);
+    expect(after[0].date).toBeNull();
+    expect(after.slice(1).map(d => d.id)).toEqual([d1.id, d2.id, d3.id]);
+  });
+
+  it('inserts at the front of a dated trip: dates stay contiguous and the trip extends', () => {
+    const trip = createTrip(testDb, userId, { start_date: '2026-03-01', end_date: '2026-03-03' });
+    const [d1, d2, d3] = orderedDays(trip.id);
+
+    const created = insertDay(trip.id, 1);
+
+    const after = orderedDays(trip.id);
+    expect(after).toHaveLength(4);
+    expect(after[0].id).toBe(created.id);
+    expect(after.map(d => d.date)).toEqual(['2026-03-01', '2026-03-02', '2026-03-03', '2026-03-04']);
+    // Old content shifted down a slot
+    expect(after.slice(1).map(d => d.id)).toEqual([d1.id, d2.id, d3.id]);
+    // Trip range extended by one day
+    const t = testDb.prepare('SELECT end_date FROM trips WHERE id = ?').get(trip.id) as { end_date: string };
+    expect(t.end_date).toBe('2026-03-04');
+  });
+});

server/tests/unit/db/atlas-region-crosswalk.test.ts

@@ -30,10 +30,14 @@ function mark(db: Database.Database, userId: number, code: string, name: string,
   ).run(userId, code, name, country);
 }
 
-// Rewind one migration and re-run so only the reconciliation (the last migration) executes.
+// The visited_regions reconciliation (#1119) is pinned at schema version 135.
+// Migrations added afterwards are appended AFTER it (append-only), so it is no
+// longer the last migration. Rewind to just before the reconciliation and
+// re-run: the later migrations are idempotent, so only the reconciliation has
+// any effect on the seeded rows here.
+const RECONCILIATION_VERSION = 135;
 function rerunLastMigration(db: Database.Database) {
-  const version = (db.prepare('SELECT version FROM schema_version').get() as { version: number }).version;
-  db.prepare('UPDATE schema_version SET version = ?').run(version - 1);
+  db.prepare('UPDATE schema_version SET version = ?').run(RECONCILIATION_VERSION - 1);
   runMigrations(db);
 }
 

server/tests/unit/nest/maps.controller.test.ts

@@ -47,7 +47,7 @@ describe('MapsController (parity with the legacy /api/maps route)', () => {
       const search = vi.fn().mockResolvedValue({ places: [], source: 'osm' });
       const res = await makeController({ search }).search(user, 'berlin', 'de');
       expect(res).toEqual({ places: [], source: 'osm' });
-      expect(search).toHaveBeenCalledWith(3, 'berlin', 'de');
+      expect(search).toHaveBeenCalledWith(3, 'berlin', 'de', undefined);
     });
 
     it('maps a service error to its status + message', async () => {

server/tests/unit/services/airtrailMapper.test.ts

@@ -0,0 +1,134 @@
+import { describe, it, expect } from 'vitest';
+import { canonicalHash, mapFlightToReservation, normalizeFlight } from '../../../src/services/airtrail/airtrailMapper';
+import type { AirtrailFlightRaw } from '../../../src/services/airtrail/airtrailClient';
+
+function airport(over: Partial<AirtrailFlightRaw['from']> = {}): NonNullable<AirtrailFlightRaw['from']> {
+  return {
+    id: 1,
+    icao: 'KJFK',
+    iata: 'JFK',
+    name: 'John F. Kennedy Intl.',
+    lat: 40.6413,
+    lon: -73.7781,
+    tz: 'America/New_York',
+    country: 'US',
+    ...over,
+  };
+}
+
+function flight(over: Partial<AirtrailFlightRaw> = {}): AirtrailFlightRaw {
+  return {
+    id: 42,
+    from: airport(),
+    to: airport({ id: 2, icao: 'EGLL', iata: 'LHR', name: 'London Heathrow', lat: 51.4706, lon: -0.4619, tz: 'Europe/London' }),
+    date: '2021-09-01',
+    datePrecision: 'day',
+    departure: '2021-09-01T23:00:00.000+00:00', // 19:00 local at JFK (EDT, UTC-4)
+    arrival: '2021-09-02T07:00:00.000+00:00', // 08:00 local at LHR (BST, UTC+1)
+    airline: { id: 1, icao: 'BAW', iata: 'BA', name: 'British Airways' },
+    flightNumber: 'BA178',
+    aircraft: { id: 1, icao: 'B772', name: 'Boeing 777' },
+    aircraftReg: 'G-VIIL',
+    flightReason: 'leisure',
+    note: 'window seat',
+    seats: [{ userId: 'u1', guestName: null, seat: 'window', seatNumber: '12A', seatClass: 'economy' }],
+    ...over,
+  };
+}
+
+describe('airtrailMapper.normalizeFlight', () => {
+  it('prefers IATA codes and exposes the picker fields', () => {
+    const n = normalizeFlight(flight());
+    expect(n).toMatchObject({
+      id: '42',
+      fromCode: 'JFK',
+      toCode: 'LHR',
+      date: '2021-09-01',
+      airline: 'BAW',
+      flightNumber: 'BA178',
+      seatClass: 'economy',
+    });
+  });
+
+  it('falls back to ICAO when IATA is missing and tolerates null airports', () => {
+    const n = normalizeFlight(flight({ from: airport({ iata: null }), to: null }));
+    expect(n.fromCode).toBe('KJFK');
+    expect(n.toCode).toBeNull();
+    expect(n.toName).toBeNull();
+  });
+});
+
+describe('airtrailMapper.mapFlightToReservation', () => {
+  it('composes airport-local times from the instant + airport tz', () => {
+    const m = mapFlightToReservation(flight());
+    // 23:00 UTC at JFK in September is 19:00 EDT; date stays the AirTrail local date.
+    expect(m.reservation_time).toBe('2021-09-01T19:00');
+    // 07:00 UTC at LHR in September is 08:00 BST.
+    expect(m.reservation_end_time).toBe('2021-09-02T08:00');
+  });
+
+  it('builds two endpoints with codes, coords and timezones', () => {
+    const m = mapFlightToReservation(flight());
+    expect(m.endpoints).toHaveLength(2);
+    expect(m.endpoints[0]).toMatchObject({ role: 'from', code: 'JFK', lat: 40.6413, timezone: 'America/New_York', local_date: '2021-09-01', local_time: '19:00' });
+    expect(m.endpoints[1]).toMatchObject({ role: 'to', code: 'LHR', timezone: 'Europe/London', local_time: '08:00' });
+    expect(m.needs_review).toBe(0);
+  });
+
+  it('titles from the flight number, else the route', () => {
+    expect(mapFlightToReservation(flight()).title).toBe('BA178');
+    expect(mapFlightToReservation(flight({ airline: null, flightNumber: null })).title).toBe('JFK → LHR');
+  });
+
+  it('carries flight metadata', () => {
+    const m = mapFlightToReservation(flight());
+    expect(m.metadata).toMatchObject({ airline: 'BAW', flight_number: 'BA178', aircraft: 'B772', aircraft_reg: 'G-VIIL', flight_reason: 'leisure', seat: '12A' });
+    expect(m.type).toBe('flight');
+    expect(m.status).toBe('confirmed');
+    expect(m.notes).toBe('window seat');
+  });
+
+  it('flags needs_review for a non-day date precision', () => {
+    expect(mapFlightToReservation(flight({ datePrecision: 'month' })).needs_review).toBe(1);
+  });
+
+  it('flags needs_review and drops the endpoint when an airport has no coordinates', () => {
+    const m = mapFlightToReservation(flight({ from: airport({ lat: null, lon: null }) }));
+    expect(m.needs_review).toBe(1);
+    expect(m.endpoints.find(e => e.role === 'from')).toBeUndefined();
+    expect(m.endpoints.find(e => e.role === 'to')).toBeDefined();
+  });
+
+  it('leaves the end time null for a partial flight with no arrival', () => {
+    const m = mapFlightToReservation(flight({ arrival: null }));
+    expect(m.reservation_end_time).toBeNull();
+    expect(m.reservation_time).toBe('2021-09-01T19:00');
+  });
+});
+
+describe('airtrailMapper.canonicalHash', () => {
+  it('is stable for the same flight', () => {
+    expect(canonicalHash(flight())).toBe(canonicalHash(flight()));
+  });
+
+  it('changes when a meaningful field changes', () => {
+    expect(canonicalHash(flight())).not.toBe(canonicalHash(flight({ flightNumber: 'BA179' })));
+    expect(canonicalHash(flight())).not.toBe(canonicalHash(flight({ note: 'aisle seat' })));
+  });
+
+  it('is independent of seat ordering', () => {
+    const a = flight({
+      seats: [
+        { userId: 'u1', guestName: null, seat: null, seatNumber: '1A', seatClass: 'economy' },
+        { userId: 'u2', guestName: null, seat: null, seatNumber: '1B', seatClass: 'economy' },
+      ],
+    });
+    const b = flight({
+      seats: [
+        { userId: 'u2', guestName: null, seat: null, seatNumber: '1B', seatClass: 'economy' },
+        { userId: 'u1', guestName: null, seat: null, seatNumber: '1A', seatClass: 'economy' },
+      ],
+    });
+    expect(canonicalHash(a)).toBe(canonicalHash(b));
+  });
+});

server/tests/unit/services/kitineraryMapper.test.ts

@@ -0,0 +1,70 @@
+import { describe, it, expect } from 'vitest';
+import { mapReservations } from '../../../src/nest/booking-import/kitinerary-mapper';
+
+const airport = (iata: string, lat: number, lng: number) => ({
+  iataCode: iata,
+  name: iata,
+  geo: { latitude: lat, longitude: lng },
+});
+
+const flight = (pnr: string, dep: any, arr: any, depTime: string, arrTime: string, flightNumber: string) => ({
+  '@type': 'FlightReservation',
+  reservationNumber: pnr,
+  reservationFor: {
+    departureAirport: dep,
+    arrivalAirport: arr,
+    departureTime: depTime,
+    arrivalTime: arrTime,
+    airline: { name: 'Lufthansa', iataCode: 'LH' },
+    flightNumber,
+  },
+});
+
+const FRA = airport('FRA', 50.04, 8.57);
+const BER = airport('BER', 52.36, 13.50);
+const HND = airport('HND', 35.55, 139.78);
+
+describe('kitinerary mapper — multi-leg flight grouping', () => {
+  it('groups two connecting same-PNR legs into one multi-leg booking', () => {
+    const { items } = mapReservations([
+      flight('ABC123', FRA, BER, '2026-06-11T10:00:00', '2026-06-11T12:00:00', 'LH 100'),
+      flight('ABC123', BER, HND, '2026-06-11T14:30:00', '2026-06-11T23:30:00', 'LH 200'),
+    ] as any, 'test.json');
+
+    expect(items).toHaveLength(1);
+    const booking = items[0];
+    expect(booking.type).toBe('flight');
+    expect(booking.endpoints).toHaveLength(3);
+    expect(booking.endpoints!.map(e => e.role)).toEqual(['from', 'stop', 'to']);
+    expect(booking.endpoints!.map(e => e.sequence)).toEqual([0, 1, 2]);
+    const meta = booking.metadata as any;
+    expect(meta.legs).toHaveLength(2);
+    expect(meta.legs[0]).toMatchObject({ from: 'FRA', to: 'BER', flight_number: 'LH 100' });
+    expect(meta.legs[1]).toMatchObject({ from: 'BER', to: 'HND', flight_number: 'LH 200' });
+    expect(meta.departure_airport).toBe('FRA');
+    expect(meta.arrival_airport).toBe('HND');
+    expect(booking.reservation_time).toContain('10:00');
+    expect(booking.reservation_end_time).toContain('23:30');
+  });
+
+  it('keeps a round trip (same PNR, multi-day gap) as two separate bookings', () => {
+    const { items } = mapReservations([
+      flight('RT999', FRA, HND, '2026-06-11T10:00:00', '2026-06-11T20:00:00', 'LH 700'),
+      flight('RT999', HND, FRA, '2026-06-20T10:00:00', '2026-06-20T18:00:00', 'LH 701'),
+    ] as any, 'test.json');
+
+    expect(items).toHaveLength(2);
+    expect((items[0].metadata as any).legs).toBeUndefined();
+    expect((items[1].metadata as any).legs).toBeUndefined();
+  });
+
+  it('leaves a single flight unchanged (two endpoints, no legs array)', () => {
+    const { items } = mapReservations([
+      flight('S1', FRA, BER, '2026-06-11T10:00:00', '2026-06-11T12:00:00', 'LH 1'),
+    ] as any, 'test.json');
+
+    expect(items).toHaveLength(1);
+    expect(items[0].endpoints).toHaveLength(2);
+    expect((items[0].metadata as any).legs).toBeUndefined();
+  });
+});

server/tests/unit/services/packingService.test.ts

@@ -275,3 +275,27 @@ describe('bulkImport with bag field', () => {
     expect(items[1].bag_id).toBe(bags[0].id);
   });
 });
+
+// ── bulkImport with quantity field ────────────────────────────────────────────
+
+describe('bulkImport with quantity field', () => {
+  it('PACK-SVC-013: bulk import respects per-item quantity, defaults to 1, and clamps out-of-range', () => {
+    const { user } = createUser(testDb);
+    const trip = createTrip(testDb, user.id);
+
+    bulkImport(trip.id, [
+      { name: 'Socks', quantity: 5 },
+      { name: 'Toothbrush' },
+      { name: 'Batteries', quantity: 9999 },
+      { name: 'Charger', quantity: 0 },
+    ]);
+
+    const byName = (n: string) =>
+      testDb.prepare('SELECT * FROM packing_items WHERE trip_id = ? AND name = ?').get(trip.id, n) as any;
+
+    expect(byName('Socks').quantity).toBe(5);
+    expect(byName('Toothbrush').quantity).toBe(1);
+    expect(byName('Batteries').quantity).toBe(999);
+    expect(byName('Charger').quantity).toBe(1);
+  });
+});

server/tests/unit/services/placeEnrichment.test.ts

@@ -0,0 +1,49 @@
+/**
+ * Unit tests for the import-enrichment match selector (#886).
+ * Covers PENRICH-001 to PENRICH-004 — the coordinate-validation guard that
+ * prevents a name search from overwriting an imported place with the wrong POI.
+ */
+import { describe, it, expect, vi } from 'vitest';
+
+// placeEnrichment pulls in the DB, websocket and maps service at import time;
+// stub them so the pure match selector can be tested in isolation.
+vi.mock('../../../src/db/database', () => ({ db: {}, getPlaceWithTags: () => null }));
+vi.mock('../../../src/websocket', () => ({ broadcast: () => {} }));
+vi.mock('../../../src/services/mapsService', () => ({
+  getMapsKey: () => null,
+  searchPlaces: async () => ({ places: [], source: 'none' }),
+  getPlacePhoto: async () => ({ photoUrl: '', attribution: null }),
+}));
+
+import { pickEnrichmentMatch } from '../../../src/services/placeEnrichment';
+
+const target = { lat: 48.85, lng: 2.35 };
+
+describe('pickEnrichmentMatch', () => {
+  it('PENRICH-001: picks the closest Google candidate within the radius', () => {
+    const candidates = [
+      { google_place_id: 'far', lat: 48.8512, lng: 2.3512 }, // ~170 m
+      { google_place_id: 'near', lat: 48.85, lng: 2.35 }, // exact
+    ];
+    const match = pickEnrichmentMatch(candidates, target);
+    expect(match?.google_place_id).toBe('near');
+  });
+
+  it('PENRICH-002: returns null when every candidate is beyond the radius', () => {
+    const candidates = [{ google_place_id: 'A', lat: 48.86, lng: 2.36 }]; // ~1.2 km
+    expect(pickEnrichmentMatch(candidates, target)).toBeNull();
+  });
+
+  it('PENRICH-003: ignores candidates without a google_place_id (e.g. OSM results)', () => {
+    const candidates = [
+      { google_place_id: null, lat: 48.85, lng: 2.35 },
+      { name: 'no id', lat: 48.85, lng: 2.35 },
+    ];
+    expect(pickEnrichmentMatch(candidates, target)).toBeNull();
+  });
+
+  it('PENRICH-004: ignores candidates with non-numeric coordinates', () => {
+    const candidates = [{ google_place_id: 'A', lat: 'x', lng: 'y' }];
+    expect(pickEnrichmentMatch(candidates as never, target)).toBeNull();
+  });
+});

shared/src/airtrail/airtrail.schema.ts

@@ -0,0 +1,79 @@
+import { z } from 'zod';
+
+/**
+ * AirTrail integration contracts (#214).
+ *
+ * AirTrail is a self-hosted flight tracker (github.com/johanohly/AirTrail).
+ * The connection is per-user (Settings → Integrations); the global on/off is the
+ * `airtrail` addon. Each user stores their instance URL + a personal Bearer API
+ * key, which only ever exposes that user's own flights.
+ */
+
+// ── Per-user connection ──────────────────────────────────────────────────────
+
+/** Placeholder the server returns instead of the real key once one is stored. */
+export const AIRTRAIL_KEY_MASK = '••••••••';
+
+export const airtrailSettingsSchema = z.object({
+  /** Instance origin, e.g. https://flights.example.com — TREK appends /api itself. */
+  url: z.string().trim().max(2048),
+  /** Bearer API key. Omitted / blank / the mask keeps the stored key unchanged. */
+  apiKey: z.string().max(512).optional(),
+  /** Allow self-signed TLS certs (common on LAN instances). */
+  allowInsecureTls: z.boolean().optional().default(false),
+});
+export type AirtrailSettings = z.infer<typeof airtrailSettingsSchema>;
+
+export const airtrailConnectionSchema = z.object({
+  url: z.string(),
+  apiKeyMasked: z.string(),
+  allowInsecureTls: z.boolean(),
+  connected: z.boolean(),
+});
+export type AirtrailConnection = z.infer<typeof airtrailConnectionSchema>;
+
+export const airtrailStatusSchema = z.object({
+  connected: z.boolean(),
+  flightCount: z.number().optional(),
+  error: z.string().optional(),
+});
+export type AirtrailStatus = z.infer<typeof airtrailStatusSchema>;
+
+// ── Flight list (picker) ─────────────────────────────────────────────────────
+
+/** A normalized AirTrail flight as surfaced to the import picker. */
+export const airtrailFlightSchema = z.object({
+  id: z.string(),
+  fromCode: z.string().nullable(),
+  fromName: z.string().nullable(),
+  toCode: z.string().nullable(),
+  toName: z.string().nullable(),
+  date: z.string().nullable(),
+  departure: z.string().nullable(),
+  arrival: z.string().nullable(),
+  airline: z.string().nullable(),
+  flightNumber: z.string().nullable(),
+  aircraft: z.string().nullable(),
+  seatClass: z.string().nullable(),
+});
+export type AirtrailFlight = z.infer<typeof airtrailFlightSchema>;
+
+// ── Import ───────────────────────────────────────────────────────────────────
+
+export const airtrailImportSchema = z.object({
+  flightIds: z.array(z.string()).min(1, 'Select at least one flight'),
+});
+export type AirtrailImport = z.infer<typeof airtrailImportSchema>;
+
+/** Per-flight outcome of an import (so the picker can show what was skipped). */
+export const airtrailImportResultSchema = z.object({
+  imported: z.array(z.string()),
+  skipped: z.array(
+    z.object({
+      flightId: z.string(),
+      reason: z.enum(['already-imported', 'already-in-trip', 'invalid']),
+      detail: z.string().optional(),
+    }),
+  ),
+});
+export type AirtrailImportResult = z.infer<typeof airtrailImportResultSchema>;

shared/src/day/day.schema.spec.ts

@@ -17,7 +17,7 @@ describe('dayCreateRequestSchema', () => {
 });
 
 describe('dayNoteCreateRequestSchema', () => {
-  it('requires non-empty text capped at 500, time capped at 150', () => {
+  it('requires non-empty text capped at 500, time capped at 250', () => {
     expect(
       dayNoteCreateRequestSchema.safeParse({ text: 'Lunch' }).success,
     ).toBe(true);
@@ -30,7 +30,7 @@ describe('dayNoteCreateRequestSchema', () => {
     expect(
       dayNoteCreateRequestSchema.safeParse({
         text: 'ok',
-        time: 'y'.repeat(151),
+        time: 'y'.repeat(251),
       }).success,
     ).toBe(false);
   });

shared/src/day/day.schema.ts

@@ -49,9 +49,17 @@ export type Day = z.infer<typeof daySchema>;
 export const dayCreateRequestSchema = z.object({
   date: z.string().optional(),
   notes: z.string().optional(),
+  // 1-based slot to insert a new empty day at (omit to append at the end).
+  position: z.number().int().positive().optional(),
 });
 export type DayCreateRequest = z.infer<typeof dayCreateRequestSchema>;
 
+/** Reorder whole days: the desired full sequence of this trip's day ids. */
+export const dayReorderRequestSchema = z.object({
+  orderedIds: z.array(z.number()),
+});
+export type DayReorderRequest = z.infer<typeof dayReorderRequestSchema>;
+
 export const dayUpdateRequestSchema = z.object({
   notes: z.string().optional(),
   title: z.string().nullable().optional(),
@@ -60,7 +68,7 @@ export type DayUpdateRequest = z.infer<typeof dayUpdateRequestSchema>;
 
 export const dayNoteCreateRequestSchema = z.object({
   text: z.string().min(1).max(500),
-  time: z.string().max(150).optional(),
+  time: z.string().max(250).optional(),
   icon: z.string().optional(),
   sort_order: z.number().optional(),
 });
@@ -68,7 +76,7 @@ export type DayNoteCreateRequest = z.infer<typeof dayNoteCreateRequestSchema>;
 
 export const dayNoteUpdateRequestSchema = z.object({
   text: z.string().max(500).optional(),
-  time: z.string().max(150).optional(),
+  time: z.string().max(250).optional(),
   icon: z.string().optional(),
   sort_order: z.number().optional(),
 });

shared/src/i18n/ar/admin.ts

@@ -360,5 +360,15 @@ const admin: TranslationStrings = {
     'إزالة جميع مفاتيح المرور لهذا المستخدم (مثلًا عند فقدان جهاز). سيظل بإمكانه تسجيل الدخول بكلمة المرور.',
   'admin.passkey.resetConfirm': 'إزالة جميع مفاتيح المرور لـ {name}؟',
   'admin.passkey.resetDone': 'تمت إزالة {count} من مفاتيح المرور',
+  'admin.defaultSettings.mapProvider': 'محرك الخرائط',
+  'admin.defaultSettings.mapProviderHint': 'الخريطة الافتراضية لجميع المستخدمين على هذا الخادم. لا يزال بإمكان كل مستخدم تجاوزها في إعداداته الخاصة.',
+  'admin.defaultSettings.providerLeaflet': 'قياسي (مجاني)',
+  'admin.defaultSettings.providerMapbox': 'Mapbox (ثلاثي الأبعاد)',
+  'admin.defaultSettings.mapboxToken': 'رمز Mapbox المشترك',
+  'admin.defaultSettings.mapboxTokenHint': 'يُستخدم لكل مستخدم لم يُدخل رمزه الخاص — حتى يحصل الخادم بأكمله على Mapbox دون مشاركة المفتاح بشكل فردي. يُخزَّن مشفّرًا.',
+  'admin.defaultSettings.mapboxStyle': 'نمط الخريطة',
+  'admin.defaultSettings.mapboxStylePlaceholder': 'اختر نمطًا…',
+  'admin.defaultSettings.mapbox3d': 'المباني والتضاريس ثلاثية الأبعاد',
+  'admin.defaultSettings.mapboxQuality': 'وضع الجودة العالية',
 };
 export default admin;

shared/src/i18n/ar/budget.ts

@@ -38,78 +38,78 @@ const budget: TranslationStrings = {
     'انقر على صورة العضو في بند الميزانية لتحديده باللون الأخضر — وهذا يعني أنه دفع. ثم تُظهر التسوية من يدين لمن وبكم.',
   'budget.netBalances': 'الأرصدة الصافية',
   'budget.categoriesLabel': 'فئات',
-  "costs.you": "You",
-  "costs.youShort": "Y",
-  "costs.youLower": "you",
-  "costs.youOwe": "You owe",
-  "costs.youOweSub": "You should pay others",
-  "costs.youreOwed": "You're owed",
-  "costs.youreOwedSub": "Others should pay you",
-  "costs.totalSpend": "Total trip spend",
-  "costs.totalSpendSub": "Across all travelers",
-  "costs.to": "To",
-  "costs.from": "From",
-  "costs.allSettled": "You're all settled up",
-  "costs.nothingOwed": "Nothing owed to you",
-  "costs.yourShare": "Your share",
-  "costs.youPaid": "You paid",
-  "costs.expenses": "Expenses",
-  "costs.entries": "{count} entries",
-  "costs.searchPlaceholder": "Search expenses…",
-  "costs.filter.all": "All",
-  "costs.filter.mine": "Paid by me",
-  "costs.filter.owed": "I'm owed",
-  "costs.addExpense": "Add expense",
-  "costs.editExpense": "Edit expense",
-  "costs.noMatch": "No expenses match your search.",
-  "costs.emptyText": "No expenses yet. Add your first one.",
-  "costs.spent": "{amount} spent",
-  "costs.noDate": "No date",
-  "costs.noOnePaid": "No one paid yet",
-  "costs.youLent": "you lent {amount}",
-  "costs.youBorrowed": "you borrowed {amount}",
-  "costs.settleUp": "Settle up",
-  "costs.history": "History",
-  "costs.everyoneSquare": "Everyone's square",
-  "costs.nothingOutstanding": "No payments outstanding right now.",
-  "costs.pay": "pay",
-  "costs.pays": "pays",
-  "costs.settle": "Settle",
-  "costs.balances": "Balances",
-  "costs.byCategory": "By category",
-  "costs.noCategories": "No expenses yet.",
-  "costs.settleHistory": "Settle history",
-  "costs.noSettlements": "No settled payments yet.",
-  "costs.paymentsSettled": "{count} payments settled",
-  "costs.paid": "paid",
-  "costs.undo": "Undo",
-  "costs.whatFor": "What was it for?",
-  "costs.namePlaceholder": "e.g. Dinner, souvenirs, gas…",
-  "costs.totalAmount": "Total amount",
-  "costs.currency": "Currency",
-  "costs.day": "Day",
-  "costs.rateLabel": "1 {from} in {to}",
-  "costs.category": "Category",
-  "costs.whoPaid": "Who paid?",
-  "costs.splitBetween": "Split equally between",
-  "costs.pickSomeone": "Pick at least one person to split with.",
-  "costs.splitSummary": "Split {count} ways · {amount} each",
-  "costs.cat.accommodation": "Accommodation",
-  "costs.cat.food": "Food & drink",
-  "costs.cat.groceries": "Groceries",
-  "costs.cat.transport": "Transport",
-  "costs.cat.flights": "Flights",
-  "costs.cat.activities": "Activities",
-  "costs.cat.sightseeing": "Sightseeing",
-  "costs.cat.shopping": "Shopping",
-  "costs.cat.fees": "Fees & tickets",
-  "costs.cat.health": "Health",
-  "costs.cat.tips": "Tips",
-  "costs.cat.other": "Other",
-  "costs.daysCount": "{count} days",
-  "costs.travelers": "{count} travelers",
-  "costs.liveRate": "live rate",
-  "costs.settleAll": "Settle all",
+  "costs.you": "أنت",
+  "costs.youShort": "أنت",
+  "costs.youLower": "أنت",
+  "costs.youOwe": "عليك",
+  "costs.youOweSub": "عليك أن تدفع للآخرين",
+  "costs.youreOwed": "لك",
+  "costs.youreOwedSub": "على الآخرين أن يدفعوا لك",
+  "costs.totalSpend": "إجمالي إنفاق الرحلة",
+  "costs.totalSpendSub": "عبر جميع المسافرين",
+  "costs.to": "إلى",
+  "costs.from": "من",
+  "costs.allSettled": "لقد سوّيت كل حساباتك",
+  "costs.nothingOwed": "لا شيء مستحق لك",
+  "costs.yourShare": "حصتك",
+  "costs.youPaid": "أنت دفعت",
+  "costs.expenses": "المصروفات",
+  "costs.entries": "{count} إدخالات",
+  "costs.searchPlaceholder": "ابحث في المصروفات…",
+  "costs.filter.all": "الكل",
+  "costs.filter.mine": "دفعتها أنا",
+  "costs.filter.owed": "مستحق لي",
+  "costs.addExpense": "إضافة مصروف",
+  "costs.editExpense": "تعديل المصروف",
+  "costs.noMatch": "لا توجد مصروفات تطابق بحثك.",
+  "costs.emptyText": "لا توجد مصروفات بعد. أضف أول مصروف لك.",
+  "costs.spent": "تم إنفاق {amount}",
+  "costs.noDate": "بدون تاريخ",
+  "costs.noOnePaid": "لم يدفع أحد بعد",
+  "costs.youLent": "أقرضت {amount}",
+  "costs.youBorrowed": "اقترضت {amount}",
+  "costs.settleUp": "تسوية الحساب",
+  "costs.history": "السجل",
+  "costs.everyoneSquare": "الجميع متعادلون",
+  "costs.nothingOutstanding": "لا توجد مدفوعات معلّقة الآن.",
+  "costs.pay": "ادفع",
+  "costs.pays": "يدفع",
+  "costs.settle": "تسوية",
+  "costs.balances": "الأرصدة",
+  "costs.byCategory": "حسب الفئة",
+  "costs.noCategories": "لا توجد مصروفات بعد.",
+  "costs.settleHistory": "سجل التسويات",
+  "costs.noSettlements": "لا توجد مدفوعات مسوّاة بعد.",
+  "costs.paymentsSettled": "تمت تسوية {count} مدفوعات",
+  "costs.paid": "مدفوع",
+  "costs.undo": "تراجع",
+  "costs.whatFor": "لأجل ماذا كان؟",
+  "costs.namePlaceholder": "مثل: عشاء، هدايا تذكارية، وقود…",
+  "costs.totalAmount": "المبلغ الإجمالي",
+  "costs.currency": "العملة",
+  "costs.day": "اليوم",
+  "costs.rateLabel": "1 {from} بـ {to}",
+  "costs.category": "الفئة",
+  "costs.whoPaid": "من دفع؟",
+  "costs.splitBetween": "تقسيم بالتساوي بين",
+  "costs.pickSomeone": "اختر شخصًا واحدًا على الأقل للتقسيم معه.",
+  "costs.splitSummary": "تقسيم على {count} · {amount} لكل واحد",
+  "costs.cat.accommodation": "الإقامة",
+  "costs.cat.food": "الطعام والشراب",
+  "costs.cat.groceries": "البقالة",
+  "costs.cat.transport": "النقل",
+  "costs.cat.flights": "الرحلات الجوية",
+  "costs.cat.activities": "الأنشطة",
+  "costs.cat.sightseeing": "معالم سياحية",
+  "costs.cat.shopping": "التسوق",
+  "costs.cat.fees": "الرسوم والتذاكر",
+  "costs.cat.health": "الصحة",
+  "costs.cat.tips": "البقشيش",
+  "costs.cat.other": "أخرى",
+  "costs.daysCount": "{count} أيام",
+  "costs.travelers": "{count} مسافرين",
+  "costs.liveRate": "سعر مباشر",
+  "costs.settleAll": "تسوية الكل",
 };
 
 export default budget;

shared/src/i18n/ar/dayplan.ts

@@ -45,5 +45,14 @@ const dayplan: TranslationStrings = {
   'dayplan.mobile.allAssigned': 'All places assigned', // en-fallback
   'dayplan.mobile.noMatch': 'No match', // en-fallback
   'dayplan.mobile.createNew': 'Create new place', // en-fallback
+  'dayplan.reorderDays': 'إعادة ترتيب الأيام',
+  'dayplan.reorderTitle': 'إعادة ترتيب الأيام',
+  'dayplan.reorderHint': 'تنتقل أماكن اليوم وملاحظاته وحجوزاته معه.',
+  'dayplan.addDay': 'إضافة يوم',
+  'dayplan.moveUp': 'تحريك لأعلى',
+  'dayplan.moveDown': 'تحريك لأسفل',
+  'dayplan.reorderUndo': 'إعادة ترتيب الأيام',
+  'dayplan.reorderError': 'تعذّر إعادة ترتيب الأيام',
+  'dayplan.addDayError': 'تعذّر إضافة يوم',
 };
 export default dayplan;

shared/src/i18n/ar/map.ts

@@ -4,5 +4,14 @@ const map: TranslationStrings = {
   'map.connections': 'الاتصالات',
   'map.showConnections': 'عرض مسارات الحجوزات',
   'map.hideConnections': 'إخفاء مسارات الحجوزات',
+  'poi.searchThisArea': 'البحث في هذه المنطقة',
+  'poi.cat.restaurants': 'مطاعم',
+  'poi.cat.cafes': 'مقاهٍ',
+  'poi.cat.bars': 'حانات وحياة ليلية',
+  'poi.cat.hotels': 'أماكن إقامة',
+  'poi.cat.sights': 'معالم',
+  'poi.cat.museums': 'متاحف وثقافة',
+  'poi.cat.nature': 'طبيعة وحدائق',
+  'poi.cat.activities': 'أنشطة',
 };
 export default map;

shared/src/i18n/ar/places.ts

@@ -86,5 +86,10 @@ const places: TranslationStrings = {
   'places.categoryCreateError': 'فشل إنشاء الفئة',
   'places.nameRequired': 'يرجى إدخال اسم',
   'places.saveError': 'فشل الحفظ',
+  'places.duplicateExists': "'{name}' موجود بالفعل في هذه الرحلة.",
+  'places.addAnyway': 'الإضافة على أي حال',
+  'places.enrichOnImport': 'إثراء الأماكن عبر Google',
+  'places.enrichOnImportHint':
+    'يبحث عن كل مكان مستورد لإضافة الصور والعنوان وبيانات الاتصال. يتطلب مفتاح خرائط Google.',
 };
 export default places;

shared/src/i18n/ar/reservations.ts

@@ -27,6 +27,11 @@ const reservations: TranslationStrings = {
   'reservations.meta.flightNumber': 'رقم الرحلة',
   'reservations.meta.from': 'من',
   'reservations.meta.to': 'إلى',
+  'reservations.layover.route': 'المسار',
+  'reservations.layover.stop': 'محطة توقف',
+  'reservations.layover.addStop': 'إضافة محطة توقف',
+  'reservations.layover.connection': 'رحلة متّصلة',
+  'reservations.layover.layover': 'توقف بيني',
   'reservations.needsReview': 'مراجعة',
   'reservations.needsReviewHint':
     'تعذّر مطابقة المطار تلقائياً — يرجى تأكيد الموقع.',
@@ -135,5 +140,22 @@ const reservations: TranslationStrings = {
   'reservations.import.unavailable': 'استيراد الحجوزات غير متاح على هذا الخادم.',
   'reservations.import.unsupportedFormat': 'صيغة ملف غير مدعومة. استخدم EML أو PDF أو PKPass أو HTML أو TXT.',
   'reservations.import.fileTooLarge': 'الملف "{name}" يتجاوز حد 10 ميغابايت.',
+  'reservations.airtrail.title': 'استيراد من AirTrail',
+  'reservations.airtrail.cta': 'AirTrail',
+  'reservations.airtrail.synced': 'AirTrail',
+  'reservations.airtrail.syncedHint': 'متزامن من AirTrail — تبقى التعديلات متزامنة في الاتجاهين.',
+  'reservations.airtrail.notSynced': 'غير متزامن',
+  'reservations.airtrail.notSyncedHint': 'تمت إزالة هذه الرحلة في AirTrail ولم تعد متزامنة.',
+  'reservations.airtrail.loadError': 'تعذّر تحميل رحلاتك من AirTrail.',
+  'reservations.airtrail.imported': 'تم استيراد {count} رحلة/رحلات',
+  'reservations.airtrail.skippedDuplicate': '{count} موجودة بالفعل في هذه الرحلة، تم تخطّيها',
+  'reservations.airtrail.nothingImported': 'لا شيء لاستيراده.',
+  'reservations.airtrail.importError': 'فشل الاستيراد. يُرجى المحاولة مرة أخرى.',
+  'reservations.airtrail.undo': 'استيراد من AirTrail',
+  'reservations.airtrail.alreadyImported': 'مُستورَد',
+  'reservations.airtrail.duringTrip': 'خلال هذه الرحلة',
+  'reservations.airtrail.otherFlights': 'رحلات أخرى',
+  'reservations.airtrail.empty': 'لم يتم العثور على أي رحلات في حساب AirTrail الخاص بك.',
+  'reservations.airtrail.importCta': 'استيراد {count}',
 };
 export default reservations;

shared/src/i18n/ar/settings.ts

@@ -317,6 +317,23 @@ const settings: TranslationStrings = {
   'settings.passkey.deviceBound': 'هذا الجهاز',
   'settings.passkey.lastUsed': 'آخر استخدام',
   'settings.passkey.neverUsed': 'لم يُستخدم قط',
+  'settings.mapPoiPill': 'استكشاف الأماكن على الخريطة',
+  'settings.mapPoiPillHint': 'أظهر شريط فئات على خريطة الرحلة للعثور على المطاعم والفنادق والمزيد القريبة من OpenStreetMap.',
+  'settings.airtrail.title': 'AirTrail',
+  'settings.airtrail.hint': 'اربط نسخة AirTrail المُستضافة ذاتيًا لاستيراد الرحلات ومزامنتها. أنشئ مفتاح API في AirTrail ضمن الإعدادات ← الأمان.',
+  'settings.airtrail.url': 'رابط النسخة',
+  'settings.airtrail.apiKey': 'مفتاح API',
+  'settings.airtrail.apiKeyPlaceholder': 'مفتاح API من نوع Bearer',
+  'settings.airtrail.apiKeyHint': 'يُنشأ في AirTrail ضمن الإعدادات ← الأمان. يُخزَّن مشفّرًا.',
+  'settings.airtrail.allowInsecureTls': 'السماح بالشهادات الموقّعة ذاتيًا',
+  'settings.airtrail.allowInsecureTlsHint': 'فعّل هذا فقط لنسخة موثوقة على شبكتك الخاصة.',
+  'settings.airtrail.connected': 'متصل',
+  'settings.airtrail.notConnected': 'غير متصل',
+  'settings.airtrail.toast.saved': 'تم حفظ اتصال AirTrail',
+  'settings.airtrail.toast.saveError': 'تعذّر حفظ الاتصال',
+  'settings.airtrail.test.button': 'اختبار الاتصال',
+  'settings.airtrail.test.success': 'متصل — تم العثور على {count} رحلة/رحلات',
+  'settings.airtrail.test.failed': 'فشل الاتصال',
 };
 
 export default settings;