diff --git a/SportsTime/Core/Models/CloudKit/CKModels.swift b/SportsTime/Core/Models/CloudKit/CKModels.swift
index 415f653..b1b3ede 100644
--- a/SportsTime/Core/Models/CloudKit/CKModels.swift
+++ b/SportsTime/Core/Models/CloudKit/CKModels.swift
@@ -632,16 +632,19 @@ struct CKCustomItineraryItem {
     static let tripIdKey = "tripId"
     static let categoryKey = "category"
     static let titleKey = "title"
-    static let anchorTypeKey = "anchorType"
-    static let anchorIdKey = "anchorId"
-    static let anchorDayKey = "anchorDay"
-    static let sortOrderKey = "sortOrder"
+    static let dayKey = "day"                    // NEW: replaces anchorDay
+    static let sortOrderDoubleKey = "sortOrderDouble"  // NEW: Double instead of Int
     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"
+    // DEPRECATED - kept for migration reads only
+    static let anchorTypeKey = "anchorType"
+    static let anchorIdKey = "anchorId"
+    static let anchorDayKey = "anchorDay"
+    static let sortOrderKey = "sortOrder"
 
     let record: CKRecord
 
@@ -658,10 +661,8 @@ struct CKCustomItineraryItem {
         record[CKCustomItineraryItem.tripIdKey] = item.tripId.uuidString
         record[CKCustomItineraryItem.categoryKey] = item.category.rawValue
         record[CKCustomItineraryItem.titleKey] = item.title
-        record[CKCustomItineraryItem.anchorTypeKey] = item.anchorType.rawValue
-        record[CKCustomItineraryItem.anchorIdKey] = item.anchorId
-        record[CKCustomItineraryItem.anchorDayKey] = item.anchorDay
-        record[CKCustomItineraryItem.sortOrderKey] = item.sortOrder
+        record[CKCustomItineraryItem.dayKey] = item.day
+        record[CKCustomItineraryItem.sortOrderDoubleKey] = item.sortOrder
         record[CKCustomItineraryItem.createdAtKey] = item.createdAt
         record[CKCustomItineraryItem.modifiedAtKey] = item.modifiedAt
         // Location fields (nil values are not stored in CloudKit)
@@ -679,15 +680,30 @@ struct CKCustomItineraryItem {
               let categoryString = record[CKCustomItineraryItem.categoryKey] as? String,
               let category = CustomItineraryItem.ItemCategory(rawValue: categoryString),
               let title = record[CKCustomItineraryItem.titleKey] as? String,
-              let anchorTypeString = record[CKCustomItineraryItem.anchorTypeKey] as? String,
-              let anchorType = CustomItineraryItem.AnchorType(rawValue: anchorTypeString),
-              let anchorDay = record[CKCustomItineraryItem.anchorDayKey] as? Int,
               let createdAt = record[CKCustomItineraryItem.createdAtKey] as? Date,
               let modifiedAt = record[CKCustomItineraryItem.modifiedAtKey] as? Date
         else { return nil }
 
-        let anchorId = record[CKCustomItineraryItem.anchorIdKey] as? String
-        let sortOrder = record[CKCustomItineraryItem.sortOrderKey] as? Int ?? 0
+        // Read new fields, with migration fallback from old fields
+        let day: Int
+        if let newDay = record[CKCustomItineraryItem.dayKey] as? Int {
+            day = newDay
+        } else if let oldDay = record[CKCustomItineraryItem.anchorDayKey] as? Int {
+            // Migration: use old anchorDay
+            day = oldDay
+        } else {
+            return nil
+        }
+
+        let sortOrder: Double
+        if let newSortOrder = record[CKCustomItineraryItem.sortOrderDoubleKey] as? Double {
+            sortOrder = newSortOrder
+        } else if let oldSortOrder = record[CKCustomItineraryItem.sortOrderKey] as? Int {
+            // Migration: convert old Int sortOrder to Double
+            sortOrder = Double(oldSortOrder)
+        } else {
+            sortOrder = 0.0
+        }
 
         // Location fields (optional - nil if not stored)
         let latitude = record[CKCustomItineraryItem.latitudeKey] as? Double
@@ -699,9 +715,7 @@ struct CKCustomItineraryItem {
             tripId: tripId,
             category: category,
             title: title,
-            anchorType: anchorType,
-            anchorId: anchorId,
-            anchorDay: anchorDay,
+            day: day,
             sortOrder: sortOrder,
             createdAt: createdAt,
             modifiedAt: modifiedAt,
diff --git a/SportsTime/Core/Models/Domain/CustomItineraryItem.swift b/SportsTime/Core/Models/Domain/CustomItineraryItem.swift
index 004705f..b49d8d5 100644
--- a/SportsTime/Core/Models/Domain/CustomItineraryItem.swift
+++ b/SportsTime/Core/Models/Domain/CustomItineraryItem.swift
@@ -11,10 +11,8 @@ struct CustomItineraryItem: Identifiable, Codable, Hashable {
     let tripId: UUID
     var category: ItemCategory
     var title: String
-    var anchorType: AnchorType
-    var anchorId: String?
-    var anchorDay: Int
-    var sortOrder: Int  // For ordering within same anchor position
+    var day: Int           // Day number (1-indexed)
+    var sortOrder: Double  // Position within day (allows insertion between items)
     let createdAt: Date
     var modifiedAt: Date
 
@@ -39,10 +37,8 @@ struct CustomItineraryItem: Identifiable, Codable, Hashable {
         tripId: UUID,
         category: ItemCategory,
         title: String,
-        anchorType: AnchorType = .startOfDay,
-        anchorId: String? = nil,
-        anchorDay: Int,
-        sortOrder: Int = 0,
+        day: Int,
+        sortOrder: Double = 0.0,
         createdAt: Date = Date(),
         modifiedAt: Date = Date(),
         latitude: Double? = nil,
@@ -53,9 +49,7 @@ struct CustomItineraryItem: Identifiable, Codable, Hashable {
         self.tripId = tripId
         self.category = category
         self.title = title
-        self.anchorType = anchorType
-        self.anchorId = anchorId
-        self.anchorDay = anchorDay
+        self.day = day
         self.sortOrder = sortOrder
         self.createdAt = createdAt
         self.modifiedAt = modifiedAt
@@ -97,10 +91,4 @@ struct CustomItineraryItem: Identifiable, Codable, Hashable {
             }
         }
     }
-
-    enum AnchorType: String, Codable {
-        case startOfDay
-        case afterGame
-        case afterTravel
-    }
 }
diff --git a/SportsTime/Core/Models/Local/SavedTrip.swift b/SportsTime/Core/Models/Local/SavedTrip.swift
index db2201e..90d67fd 100644
--- a/SportsTime/Core/Models/Local/SavedTrip.swift
+++ b/SportsTime/Core/Models/Local/SavedTrip.swift
@@ -109,9 +109,8 @@ final class LocalCustomItem {
     var tripId: UUID
     var category: String
     var title: String
-    var anchorType: String
-    var anchorId: String?
-    var anchorDay: Int
+    var day: Int
+    var sortOrder: Double
     var createdAt: Date
     var modifiedAt: Date
     var pendingSync: Bool  // True if needs to sync to CloudKit
@@ -121,9 +120,8 @@ final class LocalCustomItem {
         tripId: UUID,
         category: CustomItineraryItem.ItemCategory,
         title: String,
-        anchorType: CustomItineraryItem.AnchorType = .startOfDay,
-        anchorId: String? = nil,
-        anchorDay: Int,
+        day: Int,
+        sortOrder: Double = 0.0,
         createdAt: Date = Date(),
         modifiedAt: Date = Date(),
         pendingSync: Bool = false
@@ -132,17 +130,15 @@ final class LocalCustomItem {
         self.tripId = tripId
         self.category = category.rawValue
         self.title = title
-        self.anchorType = anchorType.rawValue
-        self.anchorId = anchorId
-        self.anchorDay = anchorDay
+        self.day = day
+        self.sortOrder = sortOrder
         self.createdAt = createdAt
         self.modifiedAt = modifiedAt
         self.pendingSync = pendingSync
     }
 
     var toItem: CustomItineraryItem? {
-        guard let category = CustomItineraryItem.ItemCategory(rawValue: category),
-              let anchorType = CustomItineraryItem.AnchorType(rawValue: anchorType)
+        guard let category = CustomItineraryItem.ItemCategory(rawValue: category)
         else { return nil }
 
         return CustomItineraryItem(
@@ -150,9 +146,8 @@ final class LocalCustomItem {
             tripId: tripId,
             category: category,
             title: title,
-            anchorType: anchorType,
-            anchorId: anchorId,
-            anchorDay: anchorDay,
+            day: day,
+            sortOrder: sortOrder,
             createdAt: createdAt,
             modifiedAt: modifiedAt
         )
@@ -164,9 +159,8 @@ final class LocalCustomItem {
             tripId: item.tripId,
             category: item.category,
             title: item.title,
-            anchorType: item.anchorType,
-            anchorId: item.anchorId,
-            anchorDay: item.anchorDay,
+            day: item.day,
+            sortOrder: item.sortOrder,
             createdAt: item.createdAt,
             modifiedAt: item.modifiedAt,
             pendingSync: pendingSync
diff --git a/SportsTime/Core/Services/CustomItemService.swift b/SportsTime/Core/Services/CustomItemService.swift
index 1c8e39e..239157b 100644
--- a/SportsTime/Core/Services/CustomItemService.swift
+++ b/SportsTime/Core/Services/CustomItemService.swift
@@ -55,10 +55,8 @@ actor CustomItemService {
         let now = Date()
         existingRecord[CKCustomItineraryItem.categoryKey] = item.category.rawValue
         existingRecord[CKCustomItineraryItem.titleKey] = item.title
-        existingRecord[CKCustomItineraryItem.anchorTypeKey] = item.anchorType.rawValue
-        existingRecord[CKCustomItineraryItem.anchorIdKey] = item.anchorId
-        existingRecord[CKCustomItineraryItem.anchorDayKey] = item.anchorDay
-        existingRecord[CKCustomItineraryItem.sortOrderKey] = item.sortOrder
+        existingRecord[CKCustomItineraryItem.dayKey] = item.day
+        existingRecord[CKCustomItineraryItem.sortOrderDoubleKey] = item.sortOrder
         existingRecord[CKCustomItineraryItem.modifiedAtKey] = now
         // Location fields (nil values clear the field in CloudKit)
         existingRecord[CKCustomItineraryItem.latitudeKey] = item.latitude
@@ -77,16 +75,16 @@ actor CustomItemService {
         }
     }
 
-    /// Batch update sortOrder for multiple items (for reordering)
+    /// Batch update day+sortOrder for multiple items (for reordering)
     func updateSortOrders(_ items: [CustomItineraryItem]) async throws {
         guard !items.isEmpty else { return }
-        print("☁️ [CloudKit] Batch updating sortOrder for \(items.count) items")
+        print("☁️ [CloudKit] Batch updating day+sortOrder for \(items.count) items")
 
         // Fetch all records
         let recordIDs = items.map { CKRecord.ID(recordName: $0.id.uuidString) }
         let fetchResults = try await publicDatabase.records(for: recordIDs)
 
-        // Update each record's sortOrder
+        // Update each record's day and sortOrder
         var recordsToSave: [CKRecord] = []
         let now = Date()
 
@@ -94,7 +92,8 @@ actor CustomItemService {
             let recordID = CKRecord.ID(recordName: item.id.uuidString)
             guard case .success(let record) = fetchResults[recordID] else { continue }
 
-            record[CKCustomItineraryItem.sortOrderKey] = item.sortOrder
+            record[CKCustomItineraryItem.dayKey] = item.day
+            record[CKCustomItineraryItem.sortOrderDoubleKey] = item.sortOrder
             record[CKCustomItineraryItem.modifiedAtKey] = now
             recordsToSave.append(record)
         }
@@ -107,7 +106,7 @@ actor CustomItemService {
             modifyOp.modifyRecordsResultBlock = { result in
                 switch result {
                 case .success:
-                    print("☁️ [CloudKit] Batch sortOrder update complete")
+                    print("☁️ [CloudKit] Batch day+sortOrder update complete")
                     continuation.resume()
                 case .failure(let error):
                     print("☁️ [CloudKit] Batch update failed: \(error)")
@@ -156,7 +155,7 @@ actor CustomItemService {
                     print("☁️ [CloudKit] Failed to parse record: \(record.recordID.recordName)")
                 }
                 return item
-            }.sorted { ($0.anchorDay, $0.sortOrder) < ($1.anchorDay, $1.sortOrder) }
+            }.sorted { ($0.day, $0.sortOrder) < ($1.day, $1.sortOrder) }
 
             print("☁️ [CloudKit] Parsed \(items.count) valid items")
             return items
diff --git a/SportsTime/Features/Trip/Views/AddItemSheet.swift b/SportsTime/Features/Trip/Views/AddItemSheet.swift
index 66fdada..e1bc46e 100644
--- a/SportsTime/Features/Trip/Views/AddItemSheet.swift
+++ b/SportsTime/Features/Trip/Views/AddItemSheet.swift
@@ -13,9 +13,7 @@ struct AddItemSheet: View {
     @Environment(\.colorScheme) private var colorScheme
 
     let tripId: UUID
-    let anchorDay: Int
-    let anchorType: CustomItineraryItem.AnchorType
-    let anchorId: String?
+    let day: Int
     let existingItem: CustomItineraryItem?
     var onSave: (CustomItineraryItem) -> Void
 
@@ -250,7 +248,7 @@ struct AddItemSheet: View {
         let item: CustomItineraryItem
 
         if let existing = existingItem {
-            // Editing existing item
+            // Editing existing item - preserve day and sortOrder
             let trimmedTitle = title.trimmingCharacters(in: .whitespaces)
             guard !trimmedTitle.isEmpty else { return }
 
@@ -259,9 +257,7 @@ struct AddItemSheet: View {
                 tripId: existing.tripId,
                 category: selectedCategory,
                 title: trimmedTitle,
-                anchorType: existing.anchorType,
-                anchorId: existing.anchorId,
-                anchorDay: existing.anchorDay,
+                day: existing.day,
                 sortOrder: existing.sortOrder,
                 createdAt: existing.createdAt,
                 modifiedAt: Date(),
@@ -274,13 +270,13 @@ struct AddItemSheet: View {
             let placeName = place.name ?? "Unknown Place"
             let coordinate = place.placemark.coordinate
 
+            // New items get sortOrder 0 (will be placed at beginning, caller can adjust)
             item = CustomItineraryItem(
                 tripId: tripId,
                 category: selectedCategory,
                 title: placeName,
-                anchorType: anchorType,
-                anchorId: anchorId,
-                anchorDay: anchorDay,
+                day: day,
+                sortOrder: 0.0,
                 latitude: coordinate.latitude,
                 longitude: coordinate.longitude,
                 address: formatAddress(for: place)
@@ -290,13 +286,13 @@ struct AddItemSheet: View {
             let trimmedTitle = title.trimmingCharacters(in: .whitespaces)
             guard !trimmedTitle.isEmpty else { return }
 
+            // New items get sortOrder 0 (will be placed at beginning, caller can adjust)
             item = CustomItineraryItem(
                 tripId: tripId,
                 category: selectedCategory,
                 title: trimmedTitle,
-                anchorType: anchorType,
-                anchorId: anchorId,
-                anchorDay: anchorDay
+                day: day,
+                sortOrder: 0.0
             )
         }
 
@@ -385,9 +381,7 @@ private struct CategoryButton: View {
 #Preview {
     AddItemSheet(
         tripId: UUID(),
-        anchorDay: 1,
-        anchorType: .startOfDay,
-        anchorId: nil,
+        day: 1,
         existingItem: nil
     ) { _ in }
 }
diff --git a/SportsTime/Features/Trip/Views/CustomItemRow.swift b/SportsTime/Features/Trip/Views/CustomItemRow.swift
index e59b406..4ca2af9 100644
--- a/SportsTime/Features/Trip/Views/CustomItemRow.swift
+++ b/SportsTime/Features/Trip/Views/CustomItemRow.swift
@@ -78,7 +78,7 @@ struct CustomItemRow: View {
                 tripId: UUID(),
                 category: .restaurant,
                 title: "Joe's BBQ - Best brisket in Texas!",
-                anchorDay: 1
+                day: 1
             ),
             onTap: {},
             onDelete: {}
@@ -88,7 +88,7 @@ struct CustomItemRow: View {
                 tripId: UUID(),
                 category: .hotel,
                 title: "Hilton Downtown",
-                anchorDay: 1
+                day: 1
             ),
             onTap: {},
             onDelete: {}
diff --git a/SportsTime/Features/Trip/Views/ItineraryTableViewController.swift b/SportsTime/Features/Trip/Views/ItineraryTableViewController.swift
index 8a7cb79..710a6f8 100644
--- a/SportsTime/Features/Trip/Views/ItineraryTableViewController.swift
+++ b/SportsTime/Features/Trip/Views/ItineraryTableViewController.swift
@@ -27,7 +27,7 @@ enum ItineraryRowItem: Identifiable, Equatable {
     case dayHeader(dayNumber: Int, date: Date, games: [RichGame])
     case travel(TravelSegment, dayNumber: Int)  // dayNumber = the day this travel is associated with
     case customItem(CustomItineraryItem)
-    case addButton(day: Int, anchorType: CustomItineraryItem.AnchorType, anchorId: String?)
+    case addButton(day: Int)  // Simplified - just needs day
 
     var id: String {
         switch self {
@@ -37,8 +37,8 @@ enum ItineraryRowItem: Identifiable, Equatable {
             return "travel:\(segment.fromLocation.name.lowercased())->\(segment.toLocation.name.lowercased())"
         case .customItem(let item):
             return "item:\(item.id.uuidString)"
-        case .addButton(let day, let anchorType, let anchorId):
-            return "add:\(day)-\(anchorType.rawValue)-\(anchorId ?? "nil")"
+        case .addButton(let day):
+            return "add:\(day)"
         }
     }
 
@@ -68,10 +68,10 @@ final class ItineraryTableViewController: UITableViewController {
 
     // Callbacks
     var onTravelMoved: ((String, Int) -> Void)?  // travelId, newDay
-    var onCustomItemMoved: ((UUID, Int, CustomItineraryItem.AnchorType, String?) -> Void)?
+    var onCustomItemMoved: ((UUID, Int, Double) -> Void)?  // itemId, newDay, newSortOrder
     var onCustomItemTapped: ((CustomItineraryItem) -> Void)?
     var onCustomItemDeleted: ((CustomItineraryItem) -> Void)?
-    var onAddButtonTapped: ((Int, CustomItineraryItem.AnchorType, String?) -> Void)?
+    var onAddButtonTapped: ((Int) -> Void)?  // Just day number
 
     // Cell reuse identifiers
     private let dayHeaderCellId = "DayHeaderCell"
@@ -234,9 +234,9 @@ final class ItineraryTableViewController: UITableViewController {
             configureCustomItemCell(cell, item: customItem)
             return cell
 
-        case .addButton(let day, let anchorType, let anchorId):
+        case .addButton(let day):
             let cell = tableView.dequeueReusableCell(withIdentifier: addButtonCellId, for: indexPath)
-            configureAddButtonCell(cell, day: day, anchorType: anchorType, anchorId: anchorId)
+            configureAddButtonCell(cell, day: day)
             return cell
         }
     }
@@ -266,8 +266,8 @@ final class ItineraryTableViewController: UITableViewController {
 
         case .customItem(let customItem):
             let destinationDay = dayNumber(forRow: destinationIndexPath.row)
-            let (anchorType, anchorId) = determineAnchor(at: destinationIndexPath.row)
-            onCustomItemMoved?(customItem.id, destinationDay, anchorType, anchorId)
+            let sortOrder = calculateSortOrder(at: destinationIndexPath.row)
+            onCustomItemMoved?(customItem.id, destinationDay, sortOrder)
 
         default:
             break
@@ -403,8 +403,8 @@ final class ItineraryTableViewController: UITableViewController {
         case .customItem(let customItem):
             onCustomItemTapped?(customItem)
 
-        case .addButton(let day, let anchorType, let anchorId):
-            onAddButtonTapped?(day, anchorType, anchorId)
+        case .addButton(let day):
+            onAddButtonTapped?(day)
 
         default:
             break
@@ -435,53 +435,64 @@ final class ItineraryTableViewController: UITableViewController {
 
     // MARK: - Helper Methods
 
-    private func determineAnchor(at row: Int) -> (CustomItineraryItem.AnchorType, String?) {
-        // Scan backwards to find the day's context
-        // Structure: travel (optional) -> dayHeader -> items
-        var foundTravel: TravelSegment?
-        var foundDayGames: [RichGame] = []
+    /// Calculate the sortOrder for an item dropped at the given row position
+    /// Uses midpoint insertion: if between sortOrder 1.0 and 2.0, returns 1.5
+    private func calculateSortOrder(at row: Int) -> Double {
+        // Find adjacent custom items to calculate midpoint
+        var prevSortOrder: Double?
+        var nextSortOrder: Double?
 
+        // Scan backwards for previous custom item in same day
         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())"
-                // 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
+            case .customItem(let item):
+                prevSortOrder = item.sortOrder
                 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)
-                }
-                // No games - check if there's travel before this day
-                // Continue scanning to find travel
-                continue
-
-            case .customItem, .addButton:
-                // Skip these, keep scanning backwards
+            case .dayHeader, .travel:
+                // Hit a boundary - no previous item in this section
+                break
+            case .addButton:
                 continue
             }
+            if prevSortOrder != nil { break }
+            // If we hit dayHeader or travel, stop scanning
+            if case .dayHeader = flatItems[i] { break }
+            if case .travel = flatItems[i] { break }
         }
 
-        // 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)
+        // Scan forwards for next custom item in same day
+        for i in row..<flatItems.count {
+            switch flatItems[i] {
+            case .customItem(let item):
+                nextSortOrder = item.sortOrder
+                break
+            case .dayHeader, .travel:
+                // Hit a boundary - no next item in this section
+                break
+            case .addButton:
+                continue
+            }
+            if nextSortOrder != nil { break }
+            // If we hit dayHeader or travel, stop scanning
+            if case .dayHeader = flatItems[i] { break }
+            if case .travel = flatItems[i] { break }
         }
 
-        return (.startOfDay, nil)
+        // Calculate appropriate sortOrder
+        switch (prevSortOrder, nextSortOrder) {
+        case (nil, nil):
+            // No adjacent items - use 1.0
+            return 1.0
+        case (let prev?, nil):
+            // After last item - use prev + 1.0
+            return prev + 1.0
+        case (nil, let next?):
+            // Before first item - use next / 2.0
+            return next / 2.0
+        case (let prev?, let next?):
+            // Between two items - use midpoint
+            return (prev + next) / 2.0
+        }
     }
 
     // MARK: - Cell Configuration
@@ -519,7 +530,7 @@ final class ItineraryTableViewController: UITableViewController {
         cell.selectionStyle = .default
     }
 
-    private func configureAddButtonCell(_ cell: UITableViewCell, day: Int, anchorType: CustomItineraryItem.AnchorType, anchorId: String?) {
+    private func configureAddButtonCell(_ cell: UITableViewCell, day: Int) {
         cell.contentConfiguration = UIHostingConfiguration {
             AddButtonRowView(colorScheme: colorScheme)
         }
diff --git a/SportsTime/Features/Trip/Views/ItineraryTableViewWrapper.swift b/SportsTime/Features/Trip/Views/ItineraryTableViewWrapper.swift
index 733658b..ba2c417 100644
--- a/SportsTime/Features/Trip/Views/ItineraryTableViewWrapper.swift
+++ b/SportsTime/Features/Trip/Views/ItineraryTableViewWrapper.swift
@@ -18,10 +18,10 @@ struct ItineraryTableViewWrapper<HeaderContent: View>: UIViewControllerRepresent
 
     // Callbacks
     var onTravelMoved: ((String, Int) -> Void)?
-    var onCustomItemMoved: ((UUID, Int, CustomItineraryItem.AnchorType, String?) -> Void)?
+    var onCustomItemMoved: ((UUID, Int, Double) -> Void)?  // itemId, newDay, newSortOrder
     var onCustomItemTapped: ((CustomItineraryItem) -> Void)?
     var onCustomItemDeleted: ((CustomItineraryItem) -> Void)?
-    var onAddButtonTapped: ((Int, CustomItineraryItem.AnchorType, String?) -> Void)?
+    var onAddButtonTapped: ((Int) -> Void)?  // Just day number
 
     init(
         trip: Trip,
@@ -30,10 +30,10 @@ struct ItineraryTableViewWrapper<HeaderContent: View>: UIViewControllerRepresent
         travelDayOverrides: [String: Int],
         @ViewBuilder headerContent: () -> HeaderContent,
         onTravelMoved: ((String, Int) -> Void)? = nil,
-        onCustomItemMoved: ((UUID, Int, CustomItineraryItem.AnchorType, String?) -> Void)? = nil,
+        onCustomItemMoved: ((UUID, Int, Double) -> Void)? = nil,
         onCustomItemTapped: ((CustomItineraryItem) -> Void)? = nil,
         onCustomItemDeleted: ((CustomItineraryItem) -> Void)? = nil,
-        onAddButtonTapped: ((Int, CustomItineraryItem.AnchorType, String?) -> Void)? = nil
+        onAddButtonTapped: ((Int) -> Void)? = nil
     ) {
         self.trip = trip
         self.games = games
@@ -159,47 +159,16 @@ struct ItineraryTableViewWrapper<HeaderContent: View>: UIViewControllerRepresent
             // Travel before this day (travel is stored on the destination day)
             let travelBefore: TravelSegment? = travelByDay[dayNum]
 
-            // Custom items after travel (if travel arrives on this day)
-            if let travelSegment = travelBefore {
-                let travelId = stableTravelAnchorId(travelSegment)
-                let itemsAfterTravel = customItems.filter {
-                    $0.anchorType == .afterTravel && $0.anchorId == travelId
-                }.sorted { $0.sortOrder < $1.sortOrder }
+            // Custom items for this day - simply filter by day and sort by sortOrder
+            let dayItems = customItems.filter { $0.day == dayNum }
+                .sorted { $0.sortOrder < $1.sortOrder }
 
-                for item in itemsAfterTravel {
-                    items.append(ItineraryRowItem.customItem(item))
-                }
-            }
-
-            // Custom items at start of day
-            let itemsAtStart = customItems.filter {
-                $0.anchorDay == dayNum && $0.anchorType == .startOfDay
-            }.sorted { $0.sortOrder < $1.sortOrder }
-
-            for item in itemsAtStart {
+            for item in dayItems {
                 items.append(ItineraryRowItem.customItem(item))
             }
 
-            // Custom items after game
-            if let lastGame = gamesOnDay.last {
-                let itemsAfterGame = customItems.filter {
-                    $0.anchorDay == dayNum && $0.anchorType == .afterGame && $0.anchorId == lastGame.game.id
-                }.sorted { $0.sortOrder < $1.sortOrder }
-
-                for item in itemsAfterGame {
-                    items.append(ItineraryRowItem.customItem(item))
-                }
-            }
-
-            // ONE Add button per day - after the last thing (game > travel > rest day)
-            if let lastGame = gamesOnDay.last {
-                items.append(ItineraryRowItem.addButton(day: dayNum, anchorType: .afterGame, anchorId: lastGame.game.id))
-            } else if let travelSegment = travelBefore {
-                let travelId = stableTravelAnchorId(travelSegment)
-                items.append(ItineraryRowItem.addButton(day: dayNum, anchorType: .afterTravel, anchorId: travelId))
-            } else {
-                items.append(ItineraryRowItem.addButton(day: dayNum, anchorType: .startOfDay, anchorId: nil))
-            }
+            // ONE Add button per day
+            items.append(ItineraryRowItem.addButton(day: dayNum))
 
             let dayData = ItineraryDayData(
                 id: dayNum,
diff --git a/SportsTime/Features/Trip/Views/TripDetailView.swift b/SportsTime/Features/Trip/Views/TripDetailView.swift
index aacbbe7..6a7213b 100644
--- a/SportsTime/Features/Trip/Views/TripDetailView.swift
+++ b/SportsTime/Features/Trip/Views/TripDetailView.swift
@@ -119,9 +119,7 @@ struct TripDetailView: View {
         .sheet(item: $addItemAnchor) { anchor in
             AddItemSheet(
                 tripId: trip.id,
-                anchorDay: anchor.day,
-                anchorType: anchor.type,
-                anchorId: anchor.anchorId,
+                day: anchor.day,
                 existingItem: nil
             ) { item in
                 Task { await saveCustomItem(item) }
@@ -130,9 +128,7 @@ struct TripDetailView: View {
         .sheet(item: $editingItem) { item in
             AddItemSheet(
                 tripId: trip.id,
-                anchorDay: item.anchorDay,
-                anchorType: item.anchorType,
-                anchorId: item.anchorId,
+                day: item.day,
                 existingItem: item
             ) { updatedItem in
                 Task { await saveCustomItem(updatedItem) }
@@ -158,7 +154,7 @@ struct TripDetailView: View {
             // 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)")
+                print("🗺️ [MapUpdate] Mappable: \(item.title) on day \(item.day), sortOrder: \(item.sortOrder)")
             }
             Task {
                 updateMapRegion()
@@ -224,10 +220,10 @@ struct TripDetailView: View {
                         await saveTravelDayOverride(travelAnchorId: travelId, displayDay: newDay)
                     }
                 },
-                onCustomItemMoved: { itemId, day, anchorType, anchorId in
+                onCustomItemMoved: { itemId, day, sortOrder in
                     Task { @MainActor in
                         guard let item = customItems.first(where: { $0.id == itemId }) else { return }
-                        await moveItemToBeginning(item, toDay: day, anchorType: anchorType, anchorId: anchorId)
+                        await moveItem(item, toDay: day, sortOrder: sortOrder)
                     }
                 },
                 onCustomItemTapped: { item in
@@ -236,8 +232,8 @@ struct TripDetailView: View {
                 onCustomItemDeleted: { item in
                     Task { await deleteCustomItem(item) }
                 },
-                onAddButtonTapped: { day, anchorType, anchorId in
-                    addItemAnchor = AddItemAnchor(day: day, type: anchorType, anchorId: anchorId)
+                onAddButtonTapped: { day in
+                    addItemAnchor = AddItemAnchor(day: day)
                 }
             )
             .ignoresSafeArea(edges: .bottom)
@@ -605,13 +601,13 @@ struct TripDetailView: View {
                 handleCustomItemDrop(providers: providers, targetItem: item)
             }
 
-        case .addButton(let day, let anchorType, let anchorId):
+        case .addButton(let day):
             VStack(spacing: 0) {
                 if isDropTarget {
                     DropTargetIndicator()
                 }
                 InlineAddButton {
-                    addItemAnchor = AddItemAnchor(day: day, type: anchorType, anchorId: anchorId)
+                    addItemAnchor = AddItemAnchor(day: day)
                 }
             }
             .onDrop(of: [.text, .plainText, .utf8PlainText], isTargeted: Binding(
@@ -628,7 +624,7 @@ struct TripDetailView: View {
                     }
                 }
             )) { providers in
-                handleAddButtonDrop(providers: providers, day: day, anchorType: anchorType, anchorId: anchorId)
+                handleAddButtonDrop(providers: providers, day: day)
             }
         }
     }
@@ -652,8 +648,12 @@ struct TripDetailView: View {
 
             Task { @MainActor in
                 let day = self.findDayForTravelSegment(segment)
-                let stableAnchorId = self.stableTravelAnchorId(segment)
-                await self.moveItemToBeginning(droppedItem, toDay: day, anchorType: .afterTravel, anchorId: stableAnchorId)
+                // Place at beginning of day (sortOrder before existing items)
+                let minSortOrder = self.customItems
+                    .filter { $0.day == day && $0.id != droppedItem.id }
+                    .map { $0.sortOrder }
+                    .min() ?? 1.0
+                await self.moveItem(droppedItem, toDay: day, sortOrder: minSortOrder / 2.0)
             }
         }
         return true
@@ -676,13 +676,19 @@ struct TripDetailView: View {
                   droppedItem.id != targetItem.id else { return }
 
             Task { @MainActor in
-                await self.moveItem(droppedItem, toDay: targetItem.anchorDay, anchorType: targetItem.anchorType, anchorId: targetItem.anchorId, beforeItem: targetItem)
+                // Place before target item using midpoint insertion
+                let itemsInDay = self.customItems.filter { $0.day == targetItem.day && $0.id != droppedItem.id }
+                    .sorted { $0.sortOrder < $1.sortOrder }
+                let targetIdx = itemsInDay.firstIndex(where: { $0.id == targetItem.id }) ?? 0
+                let prevSortOrder = targetIdx > 0 ? itemsInDay[targetIdx - 1].sortOrder : 0.0
+                let newSortOrder = (prevSortOrder + targetItem.sortOrder) / 2.0
+                await self.moveItem(droppedItem, toDay: targetItem.day, sortOrder: newSortOrder)
             }
         }
         return true
     }
 
-    private func handleAddButtonDrop(providers: [NSItemProvider], day: Int, anchorType: CustomItineraryItem.AnchorType, anchorId: String?) -> Bool {
+    private func handleAddButtonDrop(providers: [NSItemProvider], day: Int) -> Bool {
         guard let provider = providers.first, provider.canLoadObject(ofClass: NSString.self) else {
             return false
         }
@@ -698,7 +704,12 @@ struct TripDetailView: View {
                   let droppedItem = self.customItems.first(where: { $0.id == itemId }) else { return }
 
             Task { @MainActor in
-                await self.moveItemToBeginning(droppedItem, toDay: day, anchorType: anchorType, anchorId: anchorId)
+                // Calculate sortOrder: append at end of day's items
+                let maxSortOrder = self.customItems
+                    .filter { $0.day == day && $0.id != droppedItem.id }
+                    .map { $0.sortOrder }
+                    .max() ?? 0.0
+                await self.moveItem(droppedItem, toDay: day, sortOrder: maxSortOrder + 1.0)
             }
         }
         return true
@@ -719,8 +730,8 @@ struct TripDetailView: View {
             return "travel-\(segment.fromLocation.name)-\(segment.toLocation.name)"
         case .customItem(let item):
             return "item-\(item.id.uuidString)"
-        case .addButton(let day, let anchorType, _):
-            return "add-\(day)-\(anchorType.rawValue)"
+        case .addButton(let day):
+            return "add-\(day)"
         }
     }
 
@@ -747,120 +758,26 @@ struct TripDetailView: View {
         return "travel:\(from)->\(to)"
     }
 
-    private func moveItem(_ item: CustomItineraryItem, toDay day: Int, anchorType: CustomItineraryItem.AnchorType, anchorId: String?, beforeItem: CustomItineraryItem? = nil) async {
+    /// Move item to a new day and sortOrder position
+    private func moveItem(_ item: CustomItineraryItem, toDay day: Int, sortOrder: Double) async {
         var updated = item
-        updated.anchorDay = day
-        updated.anchorType = anchorType
-        updated.anchorId = anchorId
+        updated.day = day
+        updated.sortOrder = sortOrder
         updated.modifiedAt = Date()
 
-        // Calculate sortOrder
-        let itemsAtSameAnchor = customItems.filter {
-            $0.anchorDay == day &&
-            $0.anchorType == anchorType &&
-            $0.anchorId == anchorId &&
-            $0.id != item.id
-        }.sorted { $0.sortOrder < $1.sortOrder }
-
-        var itemsToSync: [CustomItineraryItem] = []
-
-        print("📍 [Move] itemsAtSameAnchor: \(itemsAtSameAnchor.map { "\($0.title) (id: \($0.id.uuidString.prefix(8)))" })")
-        if let beforeItem = beforeItem {
-            print("📍 [Move] beforeItem: \(beforeItem.title) (id: \(beforeItem.id.uuidString.prefix(8)))")
-        }
-
-        if let beforeItem = beforeItem,
-           let beforeIndex = itemsAtSameAnchor.firstIndex(where: { $0.id == beforeItem.id }) {
-            updated.sortOrder = beforeIndex
-            print("📍 [Move] Setting \(item.title) sortOrder to \(beforeIndex) (before \(beforeItem.title))")
-
-            // Shift other items and track them for syncing
-            for i in beforeIndex..<itemsAtSameAnchor.count {
-                if var shiftItem = customItems.first(where: { $0.id == itemsAtSameAnchor[i].id }) {
-                    shiftItem.sortOrder = i + 1
-                    shiftItem.modifiedAt = Date()
-                    print("📍 [Move] Shifting \(shiftItem.title) sortOrder to \(i + 1)")
-                    if let idx = customItems.firstIndex(where: { $0.id == shiftItem.id }) {
-                        customItems[idx] = shiftItem
-                    }
-                    itemsToSync.append(shiftItem)
-                }
-            }
-        } else {
-            updated.sortOrder = itemsAtSameAnchor.count
-            print("📍 [Move] Setting \(item.title) sortOrder to \(itemsAtSameAnchor.count) (end of list)")
-        }
+        print("📍 [Move] Moving \(item.title) to day \(day), sortOrder: \(sortOrder)")
 
         // Update local state
         if let idx = customItems.firstIndex(where: { $0.id == item.id }) {
             customItems[idx] = updated
         }
 
-        // Sync moved item and all shifted items to CloudKit
-        do {
-            _ = try await CustomItemService.shared.updateItem(updated)
-            print("✅ [Move] Synced \(updated.title) to day \(day), anchor: \(anchorType.rawValue), sortOrder: \(updated.sortOrder)")
-
-            // Also sync shifted items
-            for shiftItem in itemsToSync {
-                _ = try await CustomItemService.shared.updateItem(shiftItem)
-                print("✅ [Move] Synced shifted item \(shiftItem.title) with sortOrder: \(shiftItem.sortOrder)")
-            }
-        } catch {
-            print("❌ [Move] Failed to sync: \(error)")
-        }
-    }
-
-    /// Move item to the beginning of an anchor position (sortOrder 0), shifting existing items down
-    private func moveItemToBeginning(_ item: CustomItineraryItem, toDay day: Int, anchorType: CustomItineraryItem.AnchorType, anchorId: String?) async {
-        var updated = item
-        updated.anchorDay = day
-        updated.anchorType = anchorType
-        updated.anchorId = anchorId
-        updated.sortOrder = 0  // Insert at beginning
-        updated.modifiedAt = Date()
-
-        // Get existing items at this anchor position (excluding the moved item)
-        let existingItems = customItems.filter {
-            $0.anchorDay == day &&
-            $0.anchorType == anchorType &&
-            $0.anchorId == anchorId &&
-            $0.id != item.id
-        }.sorted { $0.sortOrder < $1.sortOrder }
-
-        print("📍 [MoveToBeginning] Moving \(item.title) to beginning of day \(day), anchor: \(anchorType.rawValue)")
-        print("📍 [MoveToBeginning] Existing items to shift: \(existingItems.map { "\($0.title) (order: \($0.sortOrder))" })")
-
-        // Shift all existing items down by 1
-        var itemsToSync: [CustomItineraryItem] = []
-        for (index, existingItem) in existingItems.enumerated() {
-            if var shiftItem = customItems.first(where: { $0.id == existingItem.id }) {
-                shiftItem.sortOrder = index + 1  // Shift down
-                shiftItem.modifiedAt = Date()
-                print("📍 [MoveToBeginning] Shifting \(shiftItem.title) sortOrder to \(index + 1)")
-                if let idx = customItems.firstIndex(where: { $0.id == shiftItem.id }) {
-                    customItems[idx] = shiftItem
-                }
-                itemsToSync.append(shiftItem)
-            }
-        }
-
-        // Update local state for the moved item
-        if let idx = customItems.firstIndex(where: { $0.id == item.id }) {
-            customItems[idx] = updated
-        }
-
         // Sync to CloudKit
         do {
             _ = try await CustomItemService.shared.updateItem(updated)
-            print("✅ [MoveToBeginning] Synced \(updated.title) with sortOrder: 0")
-
-            for shiftItem in itemsToSync {
-                _ = try await CustomItemService.shared.updateItem(shiftItem)
-                print("✅ [MoveToBeginning] Synced shifted item \(shiftItem.title) with sortOrder: \(shiftItem.sortOrder)")
-            }
+            print("✅ [Move] Synced \(updated.title) with day: \(day), sortOrder: \(sortOrder)")
         } catch {
-            print("❌ [MoveToBeginning] Failed to sync: \(error)")
+            print("❌ [Move] Failed to sync: \(error)")
         }
     }
 
@@ -909,60 +826,25 @@ struct TripDetailView: View {
         for (index, dayDate) in days.enumerated() {
             let dayNum = index + 1
             let gamesOnDay = gamesOn(date: dayDate)
-            let isRestDay = gamesOnDay.isEmpty
 
-            // Travel for this day (if any)
+            // Travel for this day (if any) - appears before day header
             if let travelSegment = travelByDay[dayNum] {
                 sections.append(.travel(travelSegment))
-
-                if allowCustomItems {
-                    let stableId = stableTravelAnchorId(travelSegment)
-
-                    // Add button after travel
-                    sections.append(.addButton(day: dayNum, anchorType: .afterTravel, anchorId: stableId))
-
-                    // Custom items after this travel (sorted by sortOrder)
-                    let itemsAfterTravel = customItems.filter {
-                        $0.anchorType == .afterTravel && $0.anchorId == stableId
-                    }.sorted { $0.sortOrder < $1.sortOrder }
-                    for item in itemsAfterTravel {
-                        sections.append(.customItem(item))
-                    }
-                }
-            }
-
-            // Custom items at start of day (before games or as main content for rest days)
-            if allowCustomItems {
-                let itemsAtStart = customItems.filter {
-                    $0.anchorDay == dayNum && $0.anchorType == .startOfDay
-                }.sorted { $0.sortOrder < $1.sortOrder }
-                for item in itemsAtStart {
-                    sections.append(.customItem(item))
-                }
             }
 
             // Day section - shows games or minimal rest day display
             sections.append(.day(dayNumber: dayNum, date: dayDate, games: gamesOnDay))
 
-            // Add button after day (different anchor for game days vs rest days)
+            // Custom items for this day (sorted by sortOrder)
             if allowCustomItems {
-                if isRestDay {
-                    // Rest day: add button anchored to start of day (no games to anchor to)
-                    sections.append(.addButton(day: dayNum, anchorType: .startOfDay, anchorId: nil))
-                } else if let lastGame = gamesOnDay.last {
-                    // Game day: add button anchored after last game
-                    sections.append(.addButton(day: dayNum, anchorType: .afterGame, anchorId: lastGame.game.id))
-
-                    // Custom items after this game (sorted by sortOrder)
-                    let itemsAfterGame = customItems.filter {
-                        $0.anchorDay == dayNum &&
-                        $0.anchorType == .afterGame &&
-                        $0.anchorId == lastGame.game.id
-                    }.sorted { $0.sortOrder < $1.sortOrder }
-                    for item in itemsAfterGame {
-                        sections.append(.customItem(item))
-                    }
+                let dayItems = customItems.filter { $0.day == dayNum }
+                    .sorted { $0.sortOrder < $1.sortOrder }
+                for item in dayItems {
+                    sections.append(.customItem(item))
                 }
+
+                // One add button per day
+                sections.append(.addButton(day: dayNum))
             }
         }
 
@@ -1153,13 +1035,13 @@ struct TripDetailView: View {
     /// 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 }
+        // Items are ordered by (day, sortOrder) - visual order matches route order
+        let itemsByDay = Dictionary(grouping: mappableCustomItems) { $0.day }
 
         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)")
+            for item in items.sorted(by: { $0.sortOrder < $1.sortOrder }) {
+                print("🗺️ [Waypoints]   Day \(day): \(item.title), sortOrder: \(item.sortOrder)")
             }
         }
 
@@ -1183,18 +1065,6 @@ struct TripDetailView: View {
 
             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)
@@ -1227,23 +1097,12 @@ struct TripDetailView: View {
                 }
             }
 
-            // Custom items after games
+            // Custom items for this day (ordered by sortOrder - visual order matches route)
             if let items = itemsByDay[dayNumber] {
-                let afterGameItems = items.filter { $0.anchorType == .afterGame }
-                    .sorted { $0.sortOrder < $1.sortOrder }
-                for item in afterGameItems {
+                let sortedItems = items.sorted { $0.sortOrder < $1.sortOrder }
+                for item in sortedItems {
                     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)")
+                        print("🗺️ [Waypoints]   Adding \(item.title) (sortOrder: \(item.sortOrder))")
                         waypoints.append((item.title, coord, true))
                     }
                 }
@@ -1437,7 +1296,7 @@ struct TripDetailView: View {
         let isUpdate = customItems.contains(where: { $0.id == item.id })
         print("💾 [CustomItems] Saving item: '\(item.title)' (isUpdate: \(isUpdate))")
         print("   - tripId: \(item.tripId)")
-        print("   - anchorDay: \(item.anchorDay), anchorType: \(item.anchorType.rawValue)")
+        print("   - day: \(item.day), sortOrder: \(item.sortOrder)")
 
         // Update local state immediately for responsive UI
         if isUpdate {
@@ -1518,13 +1377,12 @@ struct TripDetailView: View {
                     guard let itemId = UUID(uuidString: droppedId),
                           let item = self.customItems.first(where: { $0.id == itemId }) else { return }
 
-                    // For game days, anchor to last game; for rest days, anchor to start of day
-                    if let lastGame = gamesOnDay.last {
-                        await self.moveItemToBeginning(item, toDay: dayNumber, anchorType: .afterGame, anchorId: lastGame.game.id)
-                    } else {
-                        // Rest day - anchor to start of day
-                        await self.moveItemToBeginning(item, toDay: dayNumber, anchorType: .startOfDay, anchorId: nil)
-                    }
+                    // Append at end of day's items
+                    let maxSortOrder = self.customItems
+                        .filter { $0.day == dayNumber && $0.id != item.id }
+                        .map { $0.sortOrder }
+                        .max() ?? 0.0
+                    await self.moveItem(item, toDay: dayNumber, sortOrder: maxSortOrder + 1.0)
                 }
             }
             return true
@@ -1556,7 +1414,7 @@ enum ItinerarySection {
     case day(dayNumber: Int, date: Date, games: [RichGame])
     case travel(TravelSegment)
     case customItem(CustomItineraryItem)
-    case addButton(day: Int, anchorType: CustomItineraryItem.AnchorType, anchorId: String?)
+    case addButton(day: Int)
 
     var isCustomItem: Bool {
         if case .customItem = self { return true }
@@ -1569,8 +1427,6 @@ enum ItinerarySection {
 struct AddItemAnchor: Identifiable {
     let id = UUID()
     let day: Int
-    let type: CustomItineraryItem.AnchorType
-    let anchorId: String?
 }
 
 // MARK: - Inline Add Button
diff --git a/SportsTimeTests/Domain/CustomItineraryItemTests.swift b/SportsTimeTests/Domain/CustomItineraryItemTests.swift
index 02547cc..037c4cb 100644
--- a/SportsTimeTests/Domain/CustomItineraryItemTests.swift
+++ b/SportsTimeTests/Domain/CustomItineraryItemTests.swift
@@ -16,15 +16,44 @@ struct CustomItineraryItemTests {
             tripId: tripId,
             category: .restaurant,
             title: "Joe's BBQ",
-            anchorDay: 1
+            day: 1
         )
 
         #expect(item.tripId == tripId)
         #expect(item.category == .restaurant)
         #expect(item.title == "Joe's BBQ")
-        #expect(item.anchorType == .startOfDay)
-        #expect(item.anchorId == nil)
-        #expect(item.anchorDay == 1)
+        #expect(item.day == 1)
+        #expect(item.sortOrder == 0.0)
+    }
+
+    @Test("Item initializes with day and sortOrder")
+    func item_InitializesWithDayAndSortOrder() {
+        let tripId = UUID()
+        let item = CustomItineraryItem(
+            tripId: tripId,
+            category: .restaurant,
+            title: "Joe's BBQ",
+            day: 1,
+            sortOrder: 1.5
+        )
+
+        #expect(item.tripId == tripId)
+        #expect(item.category == .restaurant)
+        #expect(item.title == "Joe's BBQ")
+        #expect(item.day == 1)
+        #expect(item.sortOrder == 1.5)
+    }
+
+    @Test("SortOrder defaults to 0.0")
+    func sortOrder_DefaultsToZero() {
+        let item = CustomItineraryItem(
+            tripId: UUID(),
+            category: .activity,
+            title: "City Tour",
+            day: 2
+        )
+
+        #expect(item.sortOrder == 0.0)
     }
 
     @Test("Item category has correct icons")
@@ -41,9 +70,8 @@ struct CustomItineraryItemTests {
             tripId: UUID(),
             category: .hotel,
             title: "Hilton Downtown",
-            anchorType: .afterGame,
-            anchorId: "game_123",
-            anchorDay: 2
+            day: 2,
+            sortOrder: 3.5
         )
 
         let encoded = try JSONEncoder().encode(item)
@@ -51,7 +79,7 @@ struct CustomItineraryItemTests {
 
         #expect(decoded.id == item.id)
         #expect(decoded.title == item.title)
-        #expect(decoded.anchorType == .afterGame)
-        #expect(decoded.anchorId == "game_123")
+        #expect(decoded.day == 2)
+        #expect(decoded.sortOrder == 3.5)
     }
 }