WIP: map route updates and custom item drag/drop fixes (broken)

- Fixed map header not updating in ItineraryTableViewWrapper using Coordinator pattern
- Added routeVersion UUID to force Map re-render when routes change
- Fixed determineAnchor to scan backwards for correct anchor context
- Added location support to CustomItineraryItem (lat/lng/address)
- Added MapKit place search to AddItemSheet
- Added extensive debug logging for route waypoint calculation

Known issues:
- Custom items still not routing correctly after drag/drop
- Anchor type determination may still have bugs

Co-Authored-By: Claude Opus 4.5 <noreply@anthropic.com>

SportsTime/Core/Models/CloudKit/CKModels.swift

@@ -638,6 +638,10 @@ struct CKCustomItineraryItem {
     static let sortOrderKey = "sortOrder"
     static let createdAtKey = "createdAt"
     static let modifiedAtKey = "modifiedAt"
+    // Location fields for mappable items
+    static let latitudeKey = "latitude"
+    static let longitudeKey = "longitude"
+    static let addressKey = "address"
 
     let record: CKRecord
 
@@ -660,6 +664,10 @@ struct CKCustomItineraryItem {
         record[CKCustomItineraryItem.sortOrderKey] = item.sortOrder
         record[CKCustomItineraryItem.createdAtKey] = item.createdAt
         record[CKCustomItineraryItem.modifiedAtKey] = item.modifiedAt
+        // Location fields (nil values are not stored in CloudKit)
+        record[CKCustomItineraryItem.latitudeKey] = item.latitude
+        record[CKCustomItineraryItem.longitudeKey] = item.longitude
+        record[CKCustomItineraryItem.addressKey] = item.address
         self.record = record
     }
 
@@ -681,6 +689,11 @@ struct CKCustomItineraryItem {
         let anchorId = record[CKCustomItineraryItem.anchorIdKey] as? String
         let sortOrder = record[CKCustomItineraryItem.sortOrderKey] as? Int ?? 0
 
+        // Location fields (optional - nil if not stored)
+        let latitude = record[CKCustomItineraryItem.latitudeKey] as? Double
+        let longitude = record[CKCustomItineraryItem.longitudeKey] as? Double
+        let address = record[CKCustomItineraryItem.addressKey] as? String
+
         return CustomItineraryItem(
             id: itemId,
             tripId: tripId,
@@ -691,7 +704,10 @@ struct CKCustomItineraryItem {
             anchorDay: anchorDay,
             sortOrder: sortOrder,
             createdAt: createdAt,
-            modifiedAt: modifiedAt
+            modifiedAt: modifiedAt,
+            latitude: latitude,
+            longitude: longitude,
+            address: address
         )
     }
 }

SportsTime/Core/Models/Domain/CustomItineraryItem.swift

@@ -4,6 +4,7 @@
 //
 
 import Foundation
+import CoreLocation
 
 struct CustomItineraryItem: Identifiable, Codable, Hashable {
     let id: UUID
@@ -17,6 +18,22 @@ struct CustomItineraryItem: Identifiable, Codable, Hashable {
     let createdAt: Date
     var modifiedAt: Date
 
+    // Optional location for mappable items (from MapKit search)
+    var latitude: Double?
+    var longitude: Double?
+    var address: String?
+
+    /// Whether this item has a location and can be shown on the map
+    var isMappable: Bool {
+        latitude != nil && longitude != nil
+    }
+
+    /// Get coordinate if mappable
+    var coordinate: CLLocationCoordinate2D? {
+        guard let lat = latitude, let lon = longitude else { return nil }
+        return CLLocationCoordinate2D(latitude: lat, longitude: lon)
+    }
+
     init(
         id: UUID = UUID(),
         tripId: UUID,
@@ -27,7 +44,10 @@ struct CustomItineraryItem: Identifiable, Codable, Hashable {
         anchorDay: Int,
         sortOrder: Int = 0,
         createdAt: Date = Date(),
-        modifiedAt: Date = Date()
+        modifiedAt: Date = Date(),
+        latitude: Double? = nil,
+        longitude: Double? = nil,
+        address: String? = nil
     ) {
         self.id = id
         self.tripId = tripId
@@ -39,6 +59,9 @@ struct CustomItineraryItem: Identifiable, Codable, Hashable {
         self.sortOrder = sortOrder
         self.createdAt = createdAt
         self.modifiedAt = modifiedAt
+        self.latitude = latitude
+        self.longitude = longitude
+        self.address = address
     }
 
     enum ItemCategory: String, Codable, CaseIterable {

SportsTime/Core/Services/CustomItemService.swift

@@ -60,6 +60,10 @@ actor CustomItemService {
         existingRecord[CKCustomItineraryItem.anchorDayKey] = item.anchorDay
         existingRecord[CKCustomItineraryItem.sortOrderKey] = item.sortOrder
         existingRecord[CKCustomItineraryItem.modifiedAtKey] = now
+        // Location fields (nil values clear the field in CloudKit)
+        existingRecord[CKCustomItineraryItem.latitudeKey] = item.latitude
+        existingRecord[CKCustomItineraryItem.longitudeKey] = item.longitude
+        existingRecord[CKCustomItineraryItem.addressKey] = item.address
 
         do {
             try await publicDatabase.save(existingRecord)

SportsTime/Features/Trip/Views/AddItemSheet.swift

@@ -6,6 +6,7 @@
 //
 
 import SwiftUI
+import MapKit
 
 struct AddItemSheet: View {
     @Environment(\.dismiss) private var dismiss
@@ -18,10 +19,23 @@ struct AddItemSheet: View {
     let existingItem: CustomItineraryItem?
     var onSave: (CustomItineraryItem) -> Void
 
+    // Entry mode
+    enum EntryMode: String, CaseIterable {
+        case searchPlaces = "Search Places"
+        case custom = "Custom"
+    }
+
+    @State private var entryMode: EntryMode = .searchPlaces
     @State private var selectedCategory: CustomItineraryItem.ItemCategory = .restaurant
     @State private var title: String = ""
     @State private var isSaving = false
 
+    // MapKit search state
+    @State private var searchQuery = ""
+    @State private var searchResults: [MKMapItem] = []
+    @State private var selectedPlace: MKMapItem?
+    @State private var isSearching = false
+
     private var isEditing: Bool { existingItem != nil }
 
     var body: some View {
@@ -30,10 +44,25 @@ struct AddItemSheet: View {
                 // Category picker
                 categoryPicker
 
-                // Title input
-                TextField("What's the plan?", text: $title)
-                    .textFieldStyle(.roundedBorder)
-                    .font(.body)
+                // Entry mode picker (only for new items)
+                if !isEditing {
+                    Picker("Entry Mode", selection: $entryMode) {
+                        ForEach(EntryMode.allCases, id: \.self) { mode in
+                            Text(mode.rawValue).tag(mode)
+                        }
+                    }
+                    .pickerStyle(.segmented)
+                }
+
+                if entryMode == .searchPlaces && !isEditing {
+                    // MapKit search UI
+                    searchPlacesView
+                } else {
+                    // Custom text entry
+                    TextField("What's the plan?", text: $title)
+                        .textFieldStyle(.roundedBorder)
+                        .font(.body)
+                }
 
                 Spacer()
             }
@@ -49,18 +78,158 @@ struct AddItemSheet: View {
                     Button(isEditing ? "Save" : "Add") {
                         saveItem()
                     }
-                    .disabled(title.trimmingCharacters(in: .whitespaces).isEmpty || isSaving)
+                    .disabled(!canSave || isSaving)
                 }
             }
             .onAppear {
                 if let existing = existingItem {
                     selectedCategory = existing.category
                     title = existing.title
+                    // If editing a mappable item, switch to custom mode
+                    entryMode = .custom
                 }
             }
         }
     }
 
+    private var canSave: Bool {
+        if entryMode == .searchPlaces && !isEditing {
+            return selectedPlace != nil
+        } else {
+            return !title.trimmingCharacters(in: .whitespaces).isEmpty
+        }
+    }
+
+    @ViewBuilder
+    private var searchPlacesView: some View {
+        VStack(spacing: Theme.Spacing.md) {
+            // Search field
+            HStack {
+                Image(systemName: "magnifyingglass")
+                    .foregroundStyle(.secondary)
+                TextField("Search for a place...", text: $searchQuery)
+                    .textFieldStyle(.plain)
+                    .autocorrectionDisabled()
+                    .onSubmit {
+                        performSearch()
+                    }
+                if isSearching {
+                    ProgressView()
+                        .scaleEffect(0.8)
+                } else if !searchQuery.isEmpty {
+                    Button {
+                        searchQuery = ""
+                        searchResults = []
+                        selectedPlace = nil
+                    } label: {
+                        Image(systemName: "xmark.circle.fill")
+                            .foregroundStyle(.secondary)
+                    }
+                }
+            }
+            .padding(10)
+            .background(Color(.systemGray6))
+            .cornerRadius(10)
+
+            // Search results
+            if !searchResults.isEmpty {
+                ScrollView {
+                    LazyVStack(spacing: 0) {
+                        ForEach(searchResults, id: \.self) { item in
+                            PlaceResultRow(
+                                item: item,
+                                isSelected: selectedPlace == item
+                            ) {
+                                selectedPlace = item
+                            }
+                            Divider()
+                        }
+                    }
+                }
+                .frame(maxHeight: 300)
+                .background(Color(.systemBackground))
+                .cornerRadius(10)
+            } else if !searchQuery.isEmpty && !isSearching {
+                Text("No results found")
+                    .foregroundStyle(.secondary)
+                    .font(.subheadline)
+                    .padding()
+            }
+
+            // Selected place preview
+            if let place = selectedPlace {
+                selectedPlacePreview(place)
+            }
+        }
+    }
+
+    @ViewBuilder
+    private func selectedPlacePreview(_ place: MKMapItem) -> some View {
+        VStack(alignment: .leading, spacing: 4) {
+            HStack {
+                Image(systemName: "checkmark.circle.fill")
+                    .foregroundStyle(.green)
+                Text(place.name ?? "Unknown Place")
+                    .font(.headline)
+                Spacer()
+            }
+            if let address = formatAddress(for: place) {
+                Text(address)
+                    .font(.caption)
+                    .foregroundStyle(.secondary)
+            }
+        }
+        .padding()
+        .background(Color.green.opacity(0.1))
+        .cornerRadius(10)
+        .overlay(
+            RoundedRectangle(cornerRadius: 10)
+                .stroke(Color.green.opacity(0.3), lineWidth: 1)
+        )
+    }
+
+    private func performSearch() {
+        let trimmedQuery = searchQuery.trimmingCharacters(in: .whitespaces)
+        guard !trimmedQuery.isEmpty else { return }
+
+        isSearching = true
+        selectedPlace = nil
+
+        let request = MKLocalSearch.Request()
+        request.naturalLanguageQuery = trimmedQuery
+
+        let search = MKLocalSearch(request: request)
+        search.start { response, error in
+            isSearching = false
+            if let response = response {
+                searchResults = response.mapItems
+            } else {
+                searchResults = []
+            }
+        }
+    }
+
+    private func formatAddress(for item: MKMapItem) -> String? {
+        let placemark = item.placemark
+        var components: [String] = []
+
+        if let thoroughfare = placemark.thoroughfare {
+            if let subThoroughfare = placemark.subThoroughfare {
+                components.append("\(subThoroughfare) \(thoroughfare)")
+            } else {
+                components.append(thoroughfare)
+            }
+        }
+        if let locality = placemark.locality {
+            components.append(locality)
+        }
+        if let administrativeArea = placemark.administrativeArea {
+            components.append(administrativeArea)
+        }
+
+        return components.isEmpty ? nil : components.joined(separator: ", ")
+    }
+
     @ViewBuilder
     private var categoryPicker: some View {
         HStack(spacing: Theme.Spacing.md) {
@@ -76,13 +245,15 @@ struct AddItemSheet: View {
     }
 
     private func saveItem() {
-        let trimmedTitle = title.trimmingCharacters(in: .whitespaces)
-        guard !trimmedTitle.isEmpty else { return }
-
         isSaving = true
 
         let item: CustomItineraryItem
+
         if let existing = existingItem {
+            // Editing existing item
+            let trimmedTitle = title.trimmingCharacters(in: .whitespaces)
+            guard !trimmedTitle.isEmpty else { return }
+
             item = CustomItineraryItem(
                 id: existing.id,
                 tripId: existing.tripId,
@@ -91,10 +262,34 @@ struct AddItemSheet: View {
                 anchorType: existing.anchorType,
                 anchorId: existing.anchorId,
                 anchorDay: existing.anchorDay,
+                sortOrder: existing.sortOrder,
                 createdAt: existing.createdAt,
-                modifiedAt: Date()
+                modifiedAt: Date(),
+                latitude: existing.latitude,
+                longitude: existing.longitude,
+                address: existing.address
+            )
+        } else if entryMode == .searchPlaces, let place = selectedPlace {
+            // Creating from MapKit search
+            let placeName = place.name ?? "Unknown Place"
+            let coordinate = place.placemark.coordinate
+
+            item = CustomItineraryItem(
+                tripId: tripId,
+                category: selectedCategory,
+                title: placeName,
+                anchorType: anchorType,
+                anchorId: anchorId,
+                anchorDay: anchorDay,
+                latitude: coordinate.latitude,
+                longitude: coordinate.longitude,
+                address: formatAddress(for: place)
             )
         } else {
+            // Creating custom item (no location)
+            let trimmedTitle = title.trimmingCharacters(in: .whitespaces)
+            guard !trimmedTitle.isEmpty else { return }
+
             item = CustomItineraryItem(
                 tripId: tripId,
                 category: selectedCategory,
@@ -110,6 +305,55 @@ struct AddItemSheet: View {
     }
 }
 
+// MARK: - Place Result Row
+
+private struct PlaceResultRow: View {
+    let item: MKMapItem
+    let isSelected: Bool
+    let onTap: () -> Void
+
+    var body: some View {
+        Button(action: onTap) {
+            HStack {
+                VStack(alignment: .leading, spacing: 2) {
+                    Text(item.name ?? "Unknown")
+                        .font(.subheadline)
+                        .foregroundStyle(.primary)
+                    if let address = formattedAddress {
+                        Text(address)
+                            .font(.caption)
+                            .foregroundStyle(.secondary)
+                            .lineLimit(1)
+                    }
+                }
+                Spacer()
+                if isSelected {
+                    Image(systemName: "checkmark.circle.fill")
+                        .foregroundStyle(.green)
+                }
+            }
+            .padding(.vertical, 10)
+            .padding(.horizontal, 12)
+            .background(isSelected ? Color.green.opacity(0.1) : Color.clear)
+        }
+        .buttonStyle(.plain)
+    }
+
+    private var formattedAddress: String? {
+        let placemark = item.placemark
+        var components: [String] = []
+
+        if let locality = placemark.locality {
+            components.append(locality)
+        }
+        if let administrativeArea = placemark.administrativeArea {
+            components.append(administrativeArea)
+        }
+
+        return components.isEmpty ? nil : components.joined(separator: ", ")
+    }
+}
+
 // MARK: - Category Button
 
 private struct CategoryButton: View {

SportsTime/Features/Trip/Views/ItineraryTableViewController.swift

@@ -436,21 +436,51 @@ final class ItineraryTableViewController: UITableViewController {
     // MARK: - Helper Methods
 
     private func determineAnchor(at row: Int) -> (CustomItineraryItem.AnchorType, String?) {
-        if row > 0 {
-            let previousItem = flatItems[row - 1]
-            switch previousItem {
+        // Scan backwards to find the day's context
+        // Structure: travel (optional) -> dayHeader -> items
+        var foundTravel: TravelSegment?
+        var foundDayGames: [RichGame] = []
+
+        for i in stride(from: row - 1, through: 0, by: -1) {
+            switch flatItems[i] {
             case .travel(let segment, _):
+                // Found travel - if this is the first significant item, use afterTravel
+                // But only if we haven't passed a day header yet
+                if foundDayGames.isEmpty {
+                    foundTravel = segment
+                }
+                // Travel marks the boundary - stop scanning
                 let travelId = "travel:\(segment.fromLocation.name.lowercased())->\(segment.toLocation.name.lowercased())"
-                return (.afterTravel, travelId)
+                // If the drop is right after travel (no day header between), use afterTravel
+                if foundDayGames.isEmpty {
+                    return (.afterTravel, travelId)
+                }
+                // Otherwise we already passed a day header, use that context
+                break
+
             case .dayHeader(_, _, let games):
+                // Found the day header for this section
+                foundDayGames = games
+                // If day has games, items dropped after should be afterGame
                 if let lastGame = games.last {
                     return (.afterGame, lastGame.game.id)
                 }
-                return (.startOfDay, nil)
-            default:
-                return (.startOfDay, nil)
+                // No games - check if there's travel before this day
+                // Continue scanning to find travel
+                continue
+
+            case .customItem, .addButton:
+                // Skip these, keep scanning backwards
+                continue
             }
         }
+
+        // If we found travel but no games, use afterTravel
+        if let segment = foundTravel {
+            let travelId = "travel:\(segment.fromLocation.name.lowercased())->\(segment.toLocation.name.lowercased())"
+            return (.afterTravel, travelId)
+        }
+
         return (.startOfDay, nil)
     }
 
@@ -664,10 +694,29 @@ struct CustomItemRowView: View {
             Text(item.category.icon)
                 .font(.title3)
 
-            Text(item.title)
-                .font(.subheadline)
-                .foregroundStyle(Theme.textPrimary(colorScheme))
-                .lineLimit(2)
+            VStack(alignment: .leading, spacing: 2) {
+                HStack(spacing: 4) {
+                    Text(item.title)
+                        .font(.subheadline)
+                        .foregroundStyle(Theme.textPrimary(colorScheme))
+                        .lineLimit(1)
+
+                    // Map pin for mappable items
+                    if item.isMappable {
+                        Image(systemName: "mappin.circle.fill")
+                            .font(.caption)
+                            .foregroundStyle(Theme.warmOrange)
+                    }
+                }
+
+                // Address subtitle for mappable items
+                if let address = item.address, !address.isEmpty {
+                    Text(address)
+                        .font(.caption)
+                        .foregroundStyle(Theme.textMuted(colorScheme))
+                        .lineLimit(1)
+                }
+            }
 
             Spacer()
 

SportsTime/Features/Trip/Views/ItineraryTableViewWrapper.swift

@@ -47,6 +47,14 @@ struct ItineraryTableViewWrapper<HeaderContent: View>: UIViewControllerRepresent
         self.onAddButtonTapped = onAddButtonTapped
     }
 
+    func makeCoordinator() -> Coordinator {
+        Coordinator()
+    }
+
+    class Coordinator {
+        var headerHostingController: UIHostingController<HeaderContent>?
+    }
+
     func makeUIViewController(context: Context) -> ItineraryTableViewController {
         let controller = ItineraryTableViewController(style: .plain)
         controller.colorScheme = colorScheme
@@ -60,6 +68,9 @@ struct ItineraryTableViewWrapper<HeaderContent: View>: UIViewControllerRepresent
         let hostingController = UIHostingController(rootView: headerContent)
         hostingController.view.backgroundColor = .clear
 
+        // Store in coordinator for later updates
+        context.coordinator.headerHostingController = hostingController
+
         // Pre-size the header view
         hostingController.view.translatesAutoresizingMaskIntoConstraints = false
         let targetWidth = UIScreen.main.bounds.width
@@ -85,8 +96,9 @@ struct ItineraryTableViewWrapper<HeaderContent: View>: UIViewControllerRepresent
         controller.onCustomItemDeleted = onCustomItemDeleted
         controller.onAddButtonTapped = onAddButtonTapped
 
-        // Note: Don't update header content here - it causes infinite layout loops
-        // Header is set once in makeUIViewController and remains static
+        // Update header content by updating the hosting controller's rootView
+        // This avoids recreating the view hierarchy and prevents infinite loops
+        context.coordinator.headerHostingController?.rootView = headerContent
 
         let (days, validRanges) = buildItineraryData()
         controller.reloadData(days: days, travelValidRanges: validRanges)

SportsTime/Features/Trip/Views/TripDetailView.swift

@@ -28,7 +28,8 @@ struct TripDetailView: View {
     @State private var exportProgress: PDFAssetPrefetcher.PrefetchProgress?
     @State private var mapCameraPosition: MapCameraPosition = .automatic
     @State private var isSaved = false
-    @State private var routePolylines: [MKPolyline] = []
+    @State private var routeCoordinates: [[CLLocationCoordinate2D]] = []
+    @State private var mapUpdateTrigger = UUID()  // Force map refresh
     @State private var isLoadingRoutes = false
     @State private var loadedGames: [String: RichGame] = [:]
     @State private var isLoadingGames = false
@@ -150,10 +151,19 @@ struct TripDetailView: View {
         .onDisappear {
             subscriptionCancellable?.cancel()
         }
-        .onChange(of: customItems) { _, _ in
+        .onChange(of: customItems) { _, newItems in
             // Clear drag state after items update (move completed)
             draggedItem = nil
             dropTargetId = nil
+            // Recalculate routes when custom items change (mappable items affect route)
+            print("🗺️ [MapUpdate] customItems changed, count: \(newItems.count)")
+            for item in newItems where item.isMappable {
+                print("🗺️ [MapUpdate] Mappable: \(item.title) on day \(item.anchorDay), anchor: \(item.anchorType.rawValue)")
+            }
+            Task {
+                updateMapRegion()
+                await fetchDrivingRoutes()
+            }
         }
         .onChange(of: travelDayOverrides) { _, _ in
             // Clear drag state after travel move completed
@@ -320,20 +330,15 @@ struct TripDetailView: View {
 
     private var heroMapSection: some View {
         ZStack(alignment: .bottom) {
-            Map(position: $mapCameraPosition, interactionModes: []) {
-                ForEach(stopCoordinates.indices, id: \.self) { index in
-                    let stop = stopCoordinates[index]
-                    Annotation(stop.name, coordinate: stop.coordinate) {
-                        PulsingDot(color: index == 0 ? Theme.warmOrange : Theme.routeGold, size: 10)
-                    }
-                }
-
-                ForEach(routePolylines.indices, id: \.self) { index in
-                    MapPolyline(routePolylines[index])
-                        .stroke(Theme.routeGold, lineWidth: 4)
-                }
-            }
-            .mapStyle(colorScheme == .dark ? .standard(elevation: .flat, emphasis: .muted) : .standard)
+            TripMapView(
+                cameraPosition: $mapCameraPosition,
+                routeCoordinates: routeCoordinates,
+                stopCoordinates: stopCoordinates,
+                customItems: mappableCustomItems,
+                colorScheme: colorScheme,
+                routeVersion: mapUpdateTrigger
+            )
+            .id("map-\(mapUpdateTrigger)")
             .overlay(alignment: .topTrailing) {
                 // Save/Unsave heart button
                 Button {
@@ -1066,15 +1071,23 @@ struct TripDetailView: View {
     // MARK: - Map Helpers
 
     private func fetchDrivingRoutes() async {
-        let stops = stopCoordinates
-        guard stops.count >= 2 else { return }
+        // Use routeWaypoints which includes game stops + mappable custom items
+        let waypoints = routeWaypoints
+        print("🗺️ [FetchRoutes] Computing routes with \(waypoints.count) waypoints:")
+        for (index, wp) in waypoints.enumerated() {
+            print("🗺️ [FetchRoutes]   \(index): \(wp.name) (custom: \(wp.isCustomItem))")
+        }
+        guard waypoints.count >= 2 else {
+            print("🗺️ [FetchRoutes] Not enough waypoints, skipping")
+            return
+        }
 
         isLoadingRoutes = true
-        var polylines: [MKPolyline] = []
+        var allCoordinates: [[CLLocationCoordinate2D]] = []
 
-        for i in 0..<(stops.count - 1) {
-            let source = stops[i]
-            let destination = stops[i + 1]
+        for i in 0..<(waypoints.count - 1) {
+            let source = waypoints[i]
+            let destination = waypoints[i + 1]
 
             let request = MKDirections.Request()
             let sourceLocation = CLLocation(latitude: source.coordinate.latitude, longitude: source.coordinate.longitude)
@@ -1088,16 +1101,28 @@ struct TripDetailView: View {
             do {
                 let response = try await directions.calculate()
                 if let route = response.routes.first {
-                    polylines.append(route.polyline)
+                    // Extract coordinates from MKPolyline
+                    let polyline = route.polyline
+                    let pointCount = polyline.pointCount
+                    var coords: [CLLocationCoordinate2D] = []
+                    let points = polyline.points()
+                    for j in 0..<pointCount {
+                        coords.append(points[j].coordinate)
+                    }
+                    allCoordinates.append(coords)
                 }
             } catch {
-                let straightLine = MKPolyline(coordinates: [source.coordinate, destination.coordinate], count: 2)
-                polylines.append(straightLine)
+                // Fallback to straight line if directions unavailable
+                allCoordinates.append([source.coordinate, destination.coordinate])
             }
         }
 
-        routePolylines = polylines
-        isLoadingRoutes = false
+        await MainActor.run {
+            print("🗺️ [FetchRoutes] Setting \(allCoordinates.count) route segments")
+            routeCoordinates = allCoordinates
+            mapUpdateTrigger = UUID()  // Force map to re-render with new routes
+            isLoadingRoutes = false
+        }
     }
 
     private var stopCoordinates: [(name: String, coordinate: CLLocationCoordinate2D)] {
@@ -1113,10 +1138,127 @@ struct TripDetailView: View {
         }
     }
 
-    private func updateMapRegion() {
-        guard !stopCoordinates.isEmpty else { return }
+    /// Mappable custom items for display on the map
+    private var mappableCustomItems: [CustomItineraryItem] {
+        customItems.filter { $0.isMappable }
+    }
 
-        let coordinates = stopCoordinates.map(\.coordinate)
+    /// Convert stored route coordinates to MKPolyline for rendering
+    private var routePolylinesFromCoords: [MKPolyline] {
+        routeCoordinates.map { coords in
+            MKPolyline(coordinates: coords, count: coords.count)
+        }
+    }
+
+    /// Route waypoints including both game stops and mappable custom items in itinerary order
+    private var routeWaypoints: [(name: String, coordinate: CLLocationCoordinate2D, isCustomItem: Bool)] {
+        // Build an ordered list combining game stops and mappable custom items
+        // Group custom items by day
+        let itemsByDay = Dictionary(grouping: mappableCustomItems) { $0.anchorDay }
+
+        print("🗺️ [Waypoints] Building waypoints. Mappable items by day:")
+        for (day, items) in itemsByDay.sorted(by: { $0.key < $1.key }) {
+            for item in items {
+                print("🗺️ [Waypoints]   Day \(day): \(item.title), anchor: \(item.anchorType.rawValue)")
+            }
+        }
+
+        var waypoints: [(name: String, coordinate: CLLocationCoordinate2D, isCustomItem: Bool)] = []
+        let days = tripDays
+
+        print("🗺️ [Waypoints] Trip has \(days.count) days")
+
+        for (dayIndex, dayDate) in days.enumerated() {
+            let dayNumber = dayIndex + 1
+
+            // Find games on this day
+            let gamesOnDay = gamesOn(date: dayDate)
+            let calendar = Calendar.current
+            let dayCity = gamesOnDay.first?.stadium.city ?? trip.stops.first(where: { stop in
+                let arrival = calendar.startOfDay(for: stop.arrivalDate)
+                let departure = calendar.startOfDay(for: stop.departureDate)
+                let day = calendar.startOfDay(for: dayDate)
+                return day >= arrival && day <= departure
+            })?.city
+
+            print("🗺️ [Waypoints] Day \(dayNumber): city=\(dayCity ?? "none"), games=\(gamesOnDay.count)")
+
+            // Custom items at start of day (before games)
+            if let items = itemsByDay[dayNumber] {
+                let startItems = items.filter { $0.anchorType == .startOfDay }
+                    .sorted { $0.sortOrder < $1.sortOrder }
+                for item in startItems {
+                    if let coord = item.coordinate {
+                        print("🗺️ [Waypoints]   Adding \(item.title) (startOfDay)")
+                        waypoints.append((item.title, coord, true))
+                    }
+                }
+            }
+
+            // Game stop for this day (only add once per city to avoid duplicates)
+            if let city = dayCity {
+                // Check if we already have this city in waypoints (by city name or stadium name)
+                let alreadyHasCity = waypoints.contains(where: { wp in
+                    if wp.isCustomItem { return false }
+                    // Check by city name
+                    if wp.name == city { return true }
+                    // Check by stadium name for this city
+                    if let stop = trip.stops.first(where: { $0.city == city }),
+                       let stadiumId = stop.stadium,
+                       let stadium = dataProvider.stadium(for: stadiumId),
+                       wp.name == stadium.name { return true }
+                    return false
+                })
+
+                if !alreadyHasCity {
+                    if let stop = trip.stops.first(where: { $0.city == city }) {
+                        if let stadiumId = stop.stadium,
+                           let stadium = dataProvider.stadium(for: stadiumId) {
+                            print("🗺️ [Waypoints]   Adding \(stadium.name) (stadium)")
+                            waypoints.append((stadium.name, stadium.coordinate, false))
+                        } else if let coord = stop.coordinate {
+                            // No stadium ID but stop has coordinate
+                            print("🗺️ [Waypoints]   Adding \(city) (city coord)")
+                            waypoints.append((city, coord, false))
+                        }
+                    }
+                } else {
+                    print("🗺️ [Waypoints]   \(city) already in waypoints, skipping")
+                }
+            }
+
+            // Custom items after games
+            if let items = itemsByDay[dayNumber] {
+                let afterGameItems = items.filter { $0.anchorType == .afterGame }
+                    .sorted { $0.sortOrder < $1.sortOrder }
+                for item in afterGameItems {
+                    if let coord = item.coordinate {
+                        print("🗺️ [Waypoints]   Adding \(item.title) (afterGame)")
+                        waypoints.append((item.title, coord, true))
+                    }
+                }
+
+                // Custom items after travel
+                let afterTravelItems = items.filter { $0.anchorType == .afterTravel }
+                    .sorted { $0.sortOrder < $1.sortOrder }
+                for item in afterTravelItems {
+                    if let coord = item.coordinate {
+                        print("🗺️ [Waypoints]   Adding \(item.title) (afterTravel)")
+                        waypoints.append((item.title, coord, true))
+                    }
+                }
+            }
+        }
+
+        return waypoints
+    }
+
+    private func updateMapRegion() {
+        // Include both game stops and mappable custom items in region calculation
+        let waypoints = routeWaypoints
+        guard !waypoints.isEmpty else { return }
+
+        let coordinates = waypoints.map(\.coordinate)
         let lats = coordinates.map(\.latitude)
         let lons = coordinates.map(\.longitude)
 
@@ -1247,6 +1389,8 @@ struct TripDetailView: View {
 
         if let count = try? modelContext.fetchCount(descriptor), count > 0 {
             isSaved = true
+        } else {
+            isSaved = false
         }
     }
 
@@ -1277,9 +1421,6 @@ struct TripDetailView: View {
         do {
             let items = try await CustomItemService.shared.fetchItems(forTripId: trip.id)
             print("✅ [CustomItems] Loaded \(items.count) items from CloudKit")
-            for item in items {
-                print("   - \(item.title) (day \(item.anchorDay), anchor: \(item.anchorType.rawValue), sortOrder: \(item.sortOrder))")
-            }
             customItems = items
 
             // Also load travel day overrides
@@ -1804,6 +1945,65 @@ struct ShareSheet: UIViewControllerRepresentable {
     func updateUIViewController(_ uiViewController: UIActivityViewController, context: Context) {}
 }
 
+// MARK: - Trip Map View (separate component for proper state updates)
+
+struct TripMapView: View {
+    @Binding var cameraPosition: MapCameraPosition
+    let routeCoordinates: [[CLLocationCoordinate2D]]
+    let stopCoordinates: [(name: String, coordinate: CLLocationCoordinate2D)]
+    let customItems: [CustomItineraryItem]
+    let colorScheme: ColorScheme
+    let routeVersion: UUID  // Force re-render when routes change
+
+    /// Create unique ID for each route segment based on start/end coordinates
+    private func routeId(for coords: [CLLocationCoordinate2D], index: Int) -> String {
+        guard let first = coords.first, let last = coords.last else {
+            return "route-\(index)-empty"
+        }
+        return "route-\(index)-\(first.latitude)-\(first.longitude)-\(last.latitude)-\(last.longitude)"
+    }
+
+    var body: some View {
+        let _ = print("🗺️ [TripMapView] Rendering with \(routeCoordinates.count) route segments, version: \(routeVersion)")
+        Map(position: $cameraPosition, interactionModes: []) {
+            // Routes (driving directions)
+            ForEach(Array(routeCoordinates.enumerated()), id: \.offset) { index, coords in
+                let _ = print("🗺️ [TripMapView] Drawing route \(index) with \(coords.count) points")
+                if !coords.isEmpty {
+                    MapPolyline(MKPolyline(coordinates: coords, count: coords.count))
+                        .stroke(Theme.routeGold, lineWidth: 4)
+                }
+            }
+
+            // Game stop markers
+            ForEach(stopCoordinates.indices, id: \.self) { index in
+                let stop = stopCoordinates[index]
+                Annotation(stop.name, coordinate: stop.coordinate) {
+                    PulsingDot(color: index == 0 ? Theme.warmOrange : Theme.routeGold, size: 10)
+                }
+            }
+
+            // Custom item markers
+            ForEach(customItems, id: \.id) { item in
+                if let coordinate = item.coordinate {
+                    Annotation(item.title, coordinate: coordinate) {
+                        ZStack {
+                            Circle()
+                                .fill(Theme.warmOrange)
+                                .frame(width: 24, height: 24)
+                            Image(systemName: item.category.systemImage)
+                                .font(.caption2)
+                                .foregroundStyle(.white)
+                        }
+                    }
+                }
+            }
+        }
+        .id(routeVersion)  // Force Map to recreate when routes change
+        .mapStyle(colorScheme == .dark ? .standard(elevation: .flat, emphasis: .muted) : .standard)
+    }
+}
+
 #Preview {
     NavigationStack {
         TripDetailView(