diff --git a/SportsTime/Core/Models/Domain/TravelSegment.swift b/SportsTime/Core/Models/Domain/TravelSegment.swift
index 8957311..83c0e9c 100644
--- a/SportsTime/Core/Models/Domain/TravelSegment.swift
+++ b/SportsTime/Core/Models/Domain/TravelSegment.swift
@@ -58,6 +58,17 @@ struct TravelSegment: Identifiable, Codable, Hashable {
     var estimatedDrivingHours: Double { durationHours }
     var estimatedDistanceMiles: Double { distanceMiles }
 
+    /// Whether this segment requires an overnight stop based on driving time.
+    /// Segments over 8 hours of driving require rest.
+    var requiresOvernightStop: Bool {
+        durationHours > 8.0
+    }
+
+    /// Number of travel days this segment spans (accounting for daily driving limits).
+    func travelDays(maxDailyHours: Double = 8.0) -> Int {
+        max(1, Int(ceil(durationHours / maxDailyHours)))
+    }
+
     var formattedDistance: String {
         String(format: "%.0f mi", distanceMiles)
     }
diff --git a/SportsTime/Planning/Engine/GameDAGRouter.swift b/SportsTime/Planning/Engine/GameDAGRouter.swift
index e324a39..282f549 100644
--- a/SportsTime/Planning/Engine/GameDAGRouter.swift
+++ b/SportsTime/Planning/Engine/GameDAGRouter.swift
@@ -140,7 +140,8 @@ enum GameDAGRouter {
         constraints: DrivingConstraints,
         anchorGameIds: Set<String> = [],
         allowRepeatCities: Bool = true,
-        beamWidth: Int = defaultBeamWidth
+        beamWidth: Int = defaultBeamWidth,
+        routePreference: RoutePreference = .balanced
     ) -> [[Game]] {
 
         // Edge cases
@@ -254,7 +255,7 @@ enum GameDAGRouter {
         }
 
         // Step 6: Final diversity selection
-        let finalRoutes = selectDiverseRoutes(routesWithAnchors, stadiums: stadiums, maxCount: maxOptions)
+        let finalRoutes = selectDiverseRoutes(routesWithAnchors, stadiums: stadiums, maxCount: maxOptions, routePreference: routePreference)
 
         #if DEBUG
         print("🔍 DAG: Input games=\(games.count), beam=\(beam.count), withAnchors=\(routesWithAnchors.count), final=\(finalRoutes.count)")
@@ -269,6 +270,7 @@ enum GameDAGRouter {
         stadiums: [String: Stadium],
         anchorGameIds: Set<String> = [],
         allowRepeatCities: Bool = true,
+        routePreference: RoutePreference = .balanced,
         stopBuilder: ([Game], [String: Stadium]) -> [ItineraryStop]
     ) -> [[Game]] {
         let constraints = DrivingConstraints.default
@@ -277,7 +279,8 @@ enum GameDAGRouter {
             stadiums: stadiums,
             constraints: constraints,
             anchorGameIds: anchorGameIds,
-            allowRepeatCities: allowRepeatCities
+            allowRepeatCities: allowRepeatCities,
+            routePreference: routePreference
         )
     }
 
@@ -292,7 +295,8 @@ enum GameDAGRouter {
     private static func selectDiverseRoutes(
         _ routes: [[Game]],
         stadiums: [String: Stadium],
-        maxCount: Int
+        maxCount: Int,
+        routePreference: RoutePreference = .balanced
     ) -> [[Game]] {
         guard !routes.isEmpty else { return [] }
 
@@ -319,8 +323,9 @@ enum GameDAGRouter {
         let byGames = Dictionary(grouping: uniqueProfiles) { $0.gameBucket }
         for bucket in byGames.keys.sorted() {
             if selected.count >= maxCount { break }
-            if let candidates = byGames[bucket]?.sorted(by: { $0.totalMiles < $1.totalMiles }) {
-                if let best = candidates.first, !selectedKeys.contains(best.uniqueKey) {
+            if let candidates = byGames[bucket] {
+                let sorted = sortByPreference(candidates, routePreference: routePreference)
+                if let best = sorted.first(where: { !selectedKeys.contains($0.uniqueKey) }) {
                     selected.append(best)
                     selectedKeys.insert(best.uniqueKey)
                 }
@@ -331,8 +336,10 @@ enum GameDAGRouter {
         let byCities = Dictionary(grouping: uniqueProfiles) { $0.cityBucket }
         for bucket in byCities.keys.sorted() {
             if selected.count >= maxCount { break }
-            if let candidates = byCities[bucket]?.filter({ !selectedKeys.contains($0.uniqueKey) }) {
-                if let best = candidates.sorted(by: { $0.totalMiles < $1.totalMiles }).first {
+            let candidates = (byCities[bucket] ?? []).filter { !selectedKeys.contains($0.uniqueKey) }
+            if !candidates.isEmpty {
+                let sorted = sortByPreference(candidates, routePreference: routePreference)
+                if let best = sorted.first {
                     selected.append(best)
                     selectedKeys.insert(best.uniqueKey)
                 }
@@ -340,8 +347,20 @@ enum GameDAGRouter {
         }
 
         // Pass 3: Ensure at least one route per mileage bucket
+        // Bias bucket iteration order based on route preference
         let byMiles = Dictionary(grouping: uniqueProfiles) { $0.milesBucket }
-        for bucket in byMiles.keys.sorted() {
+        let milesBucketOrder: [Int]
+        switch routePreference {
+        case .direct:
+            // Prioritize low mileage buckets first
+            milesBucketOrder = byMiles.keys.sorted()
+        case .scenic:
+            // Prioritize high mileage buckets first (more cities = more scenic)
+            milesBucketOrder = byMiles.keys.sorted(by: >)
+        case .balanced:
+            milesBucketOrder = byMiles.keys.sorted()
+        }
+        for bucket in milesBucketOrder {
             if selected.count >= maxCount { break }
             if let candidates = byMiles[bucket]?.filter({ !selectedKeys.contains($0.uniqueKey) }) {
                 if let best = candidates.sorted(by: { $0.gameCount > $1.gameCount }).first {
@@ -355,8 +374,10 @@ enum GameDAGRouter {
         let byDays = Dictionary(grouping: uniqueProfiles) { $0.daysBucket }
         for bucket in byDays.keys.sorted() {
             if selected.count >= maxCount { break }
-            if let candidates = byDays[bucket]?.filter({ !selectedKeys.contains($0.uniqueKey) }) {
-                if let best = candidates.sorted(by: { $0.gameCount > $1.gameCount }).first {
+            let candidates = (byDays[bucket] ?? []).filter { !selectedKeys.contains($0.uniqueKey) }
+            if !candidates.isEmpty {
+                let sorted = sortByPreference(candidates, routePreference: routePreference)
+                if let best = sorted.first {
                     selected.append(best)
                     selectedKeys.insert(best.uniqueKey)
                 }
@@ -391,11 +412,24 @@ enum GameDAGRouter {
             if !addedAny { break }
         }
 
-        // Pass 6: If still need more, add remaining sorted by efficiency
+        // Pass 6: If still need more, add remaining sorted by route preference
         if selected.count < maxCount {
             let stillRemaining = uniqueProfiles
                 .filter { !selectedKeys.contains($0.uniqueKey) }
-                .sorted { efficiency(for: $0) > efficiency(for: $1) }
+                .sorted { a, b in
+                    switch routePreference {
+                    case .direct:
+                        // Prefer lowest mileage routes
+                        return a.totalMiles < b.totalMiles
+                    case .scenic:
+                        // Prefer routes with more unique cities
+                        if a.cityCount != b.cityCount { return a.cityCount > b.cityCount }
+                        return a.totalMiles > b.totalMiles
+                    case .balanced:
+                        // Use efficiency (games per driving hour)
+                        return efficiency(for: a) > efficiency(for: b)
+                    }
+                }
 
             for profile in stillRemaining.prefix(maxCount - selected.count) {
                 selected.append(profile)
@@ -509,6 +543,27 @@ enum GameDAGRouter {
         return Double(profile.gameCount) / drivingHours
     }
 
+    /// Sorts route profiles within a bucket based on route preference.
+    /// - Direct: lowest mileage first
+    /// - Scenic: most cities first, then highest mileage
+    /// - Balanced: best efficiency (games per driving hour)
+    private static func sortByPreference(
+        _ profiles: [RouteProfile],
+        routePreference: RoutePreference
+    ) -> [RouteProfile] {
+        profiles.sorted { a, b in
+            switch routePreference {
+            case .direct:
+                return a.totalMiles < b.totalMiles
+            case .scenic:
+                if a.cityCount != b.cityCount { return a.cityCount > b.cityCount }
+                return a.totalMiles > b.totalMiles
+            case .balanced:
+                return efficiency(for: a) > efficiency(for: b)
+            }
+        }
+    }
+
     // MARK: - Day Bucketing
 
     private static func bucketByDay(games: [Game]) -> [Int: [Game]] {
@@ -541,8 +596,14 @@ enum GameDAGRouter {
         // Time must move forward
         guard to.startTime > from.startTime else { return false }
 
-        // Same stadium = always feasible
-        if from.stadiumId == to.stadiumId { return true }
+        // Same stadium: check for sufficient time gap between games
+        if from.stadiumId == to.stadiumId {
+            let estimatedGameDurationHours: Double = 3.0
+            let departureTime = from.startTime.addingTimeInterval(estimatedGameDurationHours * 3600)
+            let hoursAvailable = to.startTime.timeIntervalSince(departureTime) / 3600.0
+            let minGapHours: Double = 1.0
+            return hoursAvailable >= minGapHours
+        }
 
         // Get stadiums
         guard let fromStadium = stadiums[from.stadiumId],
@@ -621,7 +682,7 @@ enum GameDAGRouter {
 
         guard let fromStadium = stadiums[from.stadiumId],
               let toStadium = stadiums[to.stadiumId] else {
-            return 300  // Fallback estimate
+            return 0  // Missing stadium data — cannot estimate distance
         }
 
         return TravelEstimator.haversineDistanceMiles(
diff --git a/SportsTime/Planning/Engine/ScenarioAPlanner.swift b/SportsTime/Planning/Engine/ScenarioAPlanner.swift
index afdc9d9..b7aab5d 100644
--- a/SportsTime/Planning/Engine/ScenarioAPlanner.swift
+++ b/SportsTime/Planning/Engine/ScenarioAPlanner.swift
@@ -81,14 +81,21 @@ final class ScenarioAPlanner: ScenarioPlanner {
         // Get all games that fall within the user's travel dates.
         // Sort by start time so we visit them in chronological order.
         let selectedRegions = request.preferences.selectedRegions
+        var gamesWithMissingStadium = 0
         let gamesInRange = request.allGames
             .filter { game in
                 // Must be in date range
                 guard dateRange.contains(game.startTime) else { return false }
 
+                // Track games with missing stadium data
+                guard request.stadiums[game.stadiumId] != nil else {
+                    gamesWithMissingStadium += 1
+                    return false
+                }
+
                 // Must be in selected region (if regions specified)
                 if !selectedRegions.isEmpty {
-                    guard let stadium = request.stadiums[game.stadiumId] else { return false }
+                    let stadium = request.stadiums[game.stadiumId]!
                     let gameRegion = Region.classify(longitude: stadium.coordinate.longitude)
                     return selectedRegions.contains(gameRegion)
                 }
@@ -98,10 +105,18 @@ final class ScenarioAPlanner: ScenarioPlanner {
 
         // No games? Nothing to plan.
         if gamesInRange.isEmpty {
+            var violations: [ConstraintViolation] = []
+            if gamesWithMissingStadium > 0 {
+                violations.append(ConstraintViolation(
+                    type: .missingData,
+                    description: "\(gamesWithMissingStadium) game(s) excluded due to missing stadium data",
+                    severity: .warning
+                ))
+            }
             return .failure(
                 PlanningFailure(
                     reason: .noGamesInRange,
-                    violations: []
+                    violations: violations
                 )
             )
         }
@@ -165,6 +180,7 @@ final class ScenarioAPlanner: ScenarioPlanner {
             from: filteredGames,
             stadiums: request.stadiums,
             allowRepeatCities: request.preferences.allowRepeatCities,
+            routePreference: request.preferences.routePreference,
             stopBuilder: buildStops
         )
         validRoutes.append(contentsOf: globalRoutes)
@@ -173,7 +189,8 @@ final class ScenarioAPlanner: ScenarioPlanner {
         let regionalRoutes = findRoutesPerRegion(
             games: filteredGames,
             stadiums: request.stadiums,
-            allowRepeatCities: request.preferences.allowRepeatCities
+            allowRepeatCities: request.preferences.allowRepeatCities,
+            routePreference: request.preferences.routePreference
         )
         validRoutes.append(contentsOf: regionalRoutes)
 
@@ -478,7 +495,8 @@ final class ScenarioAPlanner: ScenarioPlanner {
     private func findRoutesPerRegion(
         games: [Game],
         stadiums: [String: Stadium],
-        allowRepeatCities: Bool
+        allowRepeatCities: Bool,
+        routePreference: RoutePreference = .balanced
     ) -> [[Game]] {
         // Partition games by region
         var gamesByRegion: [Region: [Game]] = [:]
@@ -510,6 +528,7 @@ final class ScenarioAPlanner: ScenarioPlanner {
                 from: regionGames,
                 stadiums: stadiums,
                 allowRepeatCities: allowRepeatCities,
+                routePreference: routePreference,
                 stopBuilder: buildStops
             )
 
diff --git a/SportsTime/Planning/Engine/ScenarioBPlanner.swift b/SportsTime/Planning/Engine/ScenarioBPlanner.swift
index b024618..ceaddc2 100644
--- a/SportsTime/Planning/Engine/ScenarioBPlanner.swift
+++ b/SportsTime/Planning/Engine/ScenarioBPlanner.swift
@@ -163,6 +163,7 @@ final class ScenarioBPlanner: ScenarioPlanner {
                 stadiums: request.stadiums,
                 anchorGameIds: anchorGameIds,
                 allowRepeatCities: request.preferences.allowRepeatCities,
+                routePreference: request.preferences.routePreference,
                 stopBuilder: buildStops
             )
             validRoutes.append(contentsOf: globalRoutes)
@@ -172,7 +173,8 @@ final class ScenarioBPlanner: ScenarioPlanner {
                 games: gamesInRange,
                 stadiums: request.stadiums,
                 anchorGameIds: anchorGameIds,
-                allowRepeatCities: request.preferences.allowRepeatCities
+                allowRepeatCities: request.preferences.allowRepeatCities,
+                routePreference: request.preferences.routePreference
             )
             validRoutes.append(contentsOf: regionalRoutes)
 
@@ -437,7 +439,8 @@ final class ScenarioBPlanner: ScenarioPlanner {
         games: [Game],
         stadiums: [String: Stadium],
         anchorGameIds: Set<String>,
-        allowRepeatCities: Bool
+        allowRepeatCities: Bool,
+        routePreference: RoutePreference = .balanced
     ) -> [[Game]] {
         // First, determine which region(s) the anchor games are in
         var anchorRegions = Set<Region>()
@@ -482,6 +485,7 @@ final class ScenarioBPlanner: ScenarioPlanner {
                 stadiums: stadiums,
                 anchorGameIds: regionAnchorIds,
                 allowRepeatCities: allowRepeatCities,
+                routePreference: routePreference,
                 stopBuilder: buildStops
             )
 
diff --git a/SportsTime/Planning/Engine/ScenarioCPlanner.swift b/SportsTime/Planning/Engine/ScenarioCPlanner.swift
index a40187b..87e6651 100644
--- a/SportsTime/Planning/Engine/ScenarioCPlanner.swift
+++ b/SportsTime/Planning/Engine/ScenarioCPlanner.swift
@@ -248,6 +248,7 @@ final class ScenarioCPlanner: ScenarioPlanner {
                 stadiums: request.stadiums,
                 anchorGameIds: [],  // No anchors in Scenario C
                 allowRepeatCities: request.preferences.allowRepeatCities,
+                routePreference: request.preferences.routePreference,
                 stopBuilder: buildStops
             )
 
diff --git a/SportsTime/Planning/Engine/ScenarioDPlanner.swift b/SportsTime/Planning/Engine/ScenarioDPlanner.swift
index febad1a..9efc42e 100644
--- a/SportsTime/Planning/Engine/ScenarioDPlanner.swift
+++ b/SportsTime/Planning/Engine/ScenarioDPlanner.swift
@@ -215,6 +215,7 @@ final class ScenarioDPlanner: ScenarioPlanner {
             from: finalGames,
             stadiums: request.stadiums,
             allowRepeatCities: request.preferences.allowRepeatCities,
+            routePreference: request.preferences.routePreference,
             stopBuilder: buildStops
         )
         #if DEBUG
diff --git a/SportsTime/Planning/Engine/ScenarioEPlanner.swift b/SportsTime/Planning/Engine/ScenarioEPlanner.swift
index f06ca93..3f284fd 100644
--- a/SportsTime/Planning/Engine/ScenarioEPlanner.swift
+++ b/SportsTime/Planning/Engine/ScenarioEPlanner.swift
@@ -90,9 +90,16 @@ final class ScenarioEPlanner: ScenarioPlanner {
         // the user wants to visit each team's home stadium.
         var homeGamesByTeam: [String: [Game]] = [:]
         var allHomeGames: [Game] = []
+        let selectedRegions = request.preferences.selectedRegions
 
         for game in request.allGames {
             if selectedTeamIds.contains(game.homeTeamId) {
+                // Apply region filter if regions are specified
+                if !selectedRegions.isEmpty {
+                    guard let stadium = request.stadiums[game.stadiumId] else { continue }
+                    let gameRegion = Region.classify(longitude: stadium.coordinate.longitude)
+                    guard selectedRegions.contains(gameRegion) else { continue }
+                }
                 homeGamesByTeam[game.homeTeamId, default: []].append(game)
                 allHomeGames.append(game)
             }
@@ -212,6 +219,7 @@ final class ScenarioEPlanner: ScenarioPlanner {
                 stadiums: request.stadiums,
                 anchorGameIds: earliestAnchorIds,
                 allowRepeatCities: request.preferences.allowRepeatCities,
+                routePreference: request.preferences.routePreference,
                 stopBuilder: buildStops
             )
             var validRoutes = candidateRoutes.filter { route in
@@ -230,6 +238,7 @@ final class ScenarioEPlanner: ScenarioPlanner {
                         stadiums: request.stadiums,
                         anchorGameIds: latestAnchorIds,
                         allowRepeatCities: request.preferences.allowRepeatCities,
+                        routePreference: request.preferences.routePreference,
                         stopBuilder: buildStops
                     )
                     candidateRoutes.append(contentsOf: latestAnchorRoutes)
@@ -239,6 +248,7 @@ final class ScenarioEPlanner: ScenarioPlanner {
                     from: uniqueGames,
                     stadiums: request.stadiums,
                     allowRepeatCities: request.preferences.allowRepeatCities,
+                    routePreference: request.preferences.routePreference,
                     stopBuilder: buildStops
                 )
                 candidateRoutes.append(contentsOf: noAnchorRoutes)
diff --git a/SportsTime/Planning/Engine/TravelEstimator.swift b/SportsTime/Planning/Engine/TravelEstimator.swift
index 7433e9e..23b5fc0 100644
--- a/SportsTime/Planning/Engine/TravelEstimator.swift
+++ b/SportsTime/Planning/Engine/TravelEstimator.swift
@@ -17,20 +17,19 @@ import CoreLocation
 /// - Constants:
 ///   - averageSpeedMph: 60 mph
 ///   - roadRoutingFactor: 1.3 (accounts for roads vs straight-line distance)
-///   - fallbackDistanceMiles: 300 miles (when coordinates unavailable)
 ///
 /// - Invariants:
 ///   - All distance calculations are symmetric: distance(A,B) == distance(B,A)
 ///   - Road distance >= straight-line distance (roadRoutingFactor >= 1.0)
 ///   - Travel duration is always distance / averageSpeedMph
 ///   - Segments exceeding 5x maxDailyDrivingHours return nil (unreachable)
+///   - Missing coordinates → returns nil (no guessing with fallback distances)
 enum TravelEstimator {
 
     // MARK: - Constants
 
     private static let averageSpeedMph: Double = 60.0
     private static let roadRoutingFactor: Double = 1.3 // Straight line to road distance
-    private static let fallbackDistanceMiles: Double = 300.0
 
     // MARK: - Travel Estimation
 
@@ -44,7 +43,7 @@ enum TravelEstimator {
     ///
     /// - Expected Behavior:
     ///   - With valid coordinates → calculates distance using Haversine * roadRoutingFactor
-    ///   - Missing coordinates → uses fallback distance (300 miles)
+    ///   - Missing coordinates → returns nil (no fallback guessing)
     ///   - Same city (no coords) → 0 distance, 0 duration
     ///   - Driving hours > 5x maxDailyDrivingHours → returns nil
     ///   - Duration = distance / 60 mph
@@ -55,7 +54,21 @@ enum TravelEstimator {
         constraints: DrivingConstraints
     ) -> TravelSegment? {
 
-        let distanceMiles = calculateDistanceMiles(from: from, to: to)
+        // If either stop is missing coordinates, the segment is infeasible
+        // (unless same city, which returns 0 distance)
+        guard let distanceMiles = calculateDistanceMiles(from: from, to: to) else {
+            // Same city with no coords: zero-distance segment
+            if from.city == to.city {
+                return TravelSegment(
+                    fromLocation: from.location,
+                    toLocation: to.location,
+                    travelMode: .drive,
+                    distanceMeters: 0,
+                    durationSeconds: 0
+                )
+            }
+            return nil
+        }
         let drivingHours = distanceMiles / averageSpeedMph
 
         // Maximum allowed: 5 days of driving as a conservative hard cap.
@@ -126,22 +139,20 @@ enum TravelEstimator {
     /// - Parameters:
     ///   - from: Origin stop
     ///   - to: Destination stop
-    /// - Returns: Distance in miles
+    /// - Returns: Distance in miles, or nil if coordinates are missing
     ///
     /// - Expected Behavior:
     ///   - Both have coordinates → Haversine distance * 1.3
-    ///   - Either missing coordinates → fallback distance
-    ///   - Same city (no coords) → 0 miles
-    ///   - Different cities (no coords) → 300 miles
+    ///   - Either missing coordinates → nil (no fallback guessing)
     static func calculateDistanceMiles(
         from: ItineraryStop,
         to: ItineraryStop
-    ) -> Double {
-        if let fromCoord = from.coordinate,
-           let toCoord = to.coordinate {
-            return haversineDistanceMiles(from: fromCoord, to: toCoord) * roadRoutingFactor
+    ) -> Double? {
+        guard let fromCoord = from.coordinate,
+              let toCoord = to.coordinate else {
+            return nil
         }
-        return estimateFallbackDistance(from: from, to: to)
+        return haversineDistanceMiles(from: fromCoord, to: toCoord) * roadRoutingFactor
     }
 
     /// Calculates straight-line distance in miles using Haversine formula.
@@ -206,24 +217,19 @@ enum TravelEstimator {
         return earthRadiusMeters * c
     }
 
-    /// Fallback distance when coordinates aren't available.
+    // MARK: - Overnight Stop Detection
+
+    /// Determines if a travel segment requires an overnight stop.
     ///
     /// - Parameters:
-    ///   - from: Origin stop
-    ///   - to: Destination stop
-    /// - Returns: Estimated distance in miles
-    ///
-    /// - Expected Behavior:
-    ///   - Same city → 0 miles
-    ///   - Different cities → 300 miles (fallback constant)
-    static func estimateFallbackDistance(
-        from: ItineraryStop,
-        to: ItineraryStop
-    ) -> Double {
-        if from.city == to.city {
-            return 0
-        }
-        return fallbackDistanceMiles
+    ///   - segment: The travel segment to evaluate
+    ///   - constraints: Driving constraints (max daily hours)
+    /// - Returns: true if driving hours exceed the daily limit
+    static func requiresOvernightStop(
+        segment: TravelSegment,
+        constraints: DrivingConstraints
+    ) -> Bool {
+        segment.estimatedDrivingHours > constraints.maxDailyDrivingHours
     }
 
     // MARK: - Travel Days
diff --git a/SportsTime/Planning/Engine/TripPlanningEngine.swift b/SportsTime/Planning/Engine/TripPlanningEngine.swift
index fe0b511..fabf20b 100644
--- a/SportsTime/Planning/Engine/TripPlanningEngine.swift
+++ b/SportsTime/Planning/Engine/TripPlanningEngine.swift
@@ -24,6 +24,10 @@ import Foundation
 ///
 final class TripPlanningEngine {
 
+    /// Warnings generated during the last planning run.
+    /// Populated when options are filtered out but valid results remain.
+    private(set) var warnings: [ConstraintViolation] = []
+
     /// Plans itineraries based on the request inputs.
     /// Automatically detects which scenario applies and delegates to the appropriate planner.
     ///
@@ -31,6 +35,32 @@ final class TripPlanningEngine {
     /// - Returns: Ranked itineraries on success, or explicit failure with reason
     func planItineraries(request: PlanningRequest) -> ItineraryResult {
 
+        // Reset warnings from previous run
+        warnings = []
+
+        // Warn on empty sports set
+        if request.preferences.sports.isEmpty {
+            warnings.append(ConstraintViolation(
+                type: .missingData,
+                description: "No sports selected — results may be empty",
+                severity: .warning
+            ))
+        }
+
+        // Validate date range is not inverted
+        if request.preferences.endDate < request.preferences.startDate {
+            return .failure(PlanningFailure(
+                reason: .missingDateRange,
+                violations: [
+                    ConstraintViolation(
+                        type: .dateRange,
+                        description: "End date is before start date",
+                        severity: .error
+                    )
+                ]
+            ))
+        }
+
         // Detect scenario and get the appropriate planner
         let planner = ScenarioPlannerFactory.planner(for: request)
 
@@ -45,6 +75,7 @@ final class TripPlanningEngine {
 
     /// Applies allowRepeatCities filter after scenario planners return.
     /// Note: Region filtering is done during game selection in scenario planners.
+    /// Tracks excluded options as warnings when valid results remain.
     private func applyPreferenceFilters(
         to result: ItineraryResult,
         request: PlanningRequest
@@ -56,6 +87,7 @@ final class TripPlanningEngine {
         var options = originalOptions
 
         // Filter repeat cities (this is enforced during beam search, but double-check here)
+        let preRepeatCount = options.count
         options = RouteFilters.filterRepeatCities(
             options,
             allow: request.preferences.allowRepeatCities
@@ -68,7 +100,77 @@ final class TripPlanningEngine {
             ))
         }
 
-        // Region filtering is applied during game selection in scenario planners
+        let repeatCityExcluded = preRepeatCount - options.count
+        if repeatCityExcluded > 0 {
+            warnings.append(ConstraintViolation(
+                type: .general,
+                description: "\(repeatCityExcluded) route(s) excluded for visiting the same city on multiple days",
+                severity: .warning
+            ))
+        }
+
+        // Must-stop filter: ensure all must-stop cities appear in routes
+        if !request.preferences.mustStopLocations.isEmpty {
+            let requiredCities = request.preferences.mustStopLocations
+                .map { $0.name.lowercased() }
+                .filter { !$0.isEmpty }
+
+            if !requiredCities.isEmpty {
+                let preMustStopCount = options.count
+                options = options.filter { option in
+                    let tripCities = Set(option.stops.map { $0.city.lowercased() })
+                    return requiredCities.allSatisfy { tripCities.contains($0) }
+                }
+
+                if options.isEmpty {
+                    return .failure(PlanningFailure(
+                        reason: .noValidRoutes,
+                        violations: [
+                            ConstraintViolation(
+                                type: .mustStop,
+                                description: "No routes include all must-stop cities",
+                                severity: .error
+                            )
+                        ]
+                    ))
+                }
+
+                let mustStopExcluded = preMustStopCount - options.count
+                if mustStopExcluded > 0 {
+                    let cityList = requiredCities.joined(separator: ", ")
+                    warnings.append(ConstraintViolation(
+                        type: .mustStop,
+                        description: "\(mustStopExcluded) route(s) excluded for missing must-stop cities: \(cityList)",
+                        severity: .warning
+                    ))
+                }
+            }
+        }
+
+        // Validate travel segments: filter out invalid options
+        let preValidCount = options.count
+        options = options.filter { $0.isValid }
+        if options.isEmpty {
+            return .failure(PlanningFailure(
+                reason: .noValidRoutes,
+                violations: [
+                    ConstraintViolation(
+                        type: .segmentMismatch,
+                        description: "No valid itineraries could be built",
+                        severity: .error
+                    )
+                ]
+            ))
+        }
+
+        let segmentExcluded = preValidCount - options.count
+        if segmentExcluded > 0 {
+            warnings.append(ConstraintViolation(
+                type: .segmentMismatch,
+                description: "\(segmentExcluded) route(s) excluded due to invalid travel segments",
+                severity: .warning
+            ))
+        }
 
         return .success(options)
     }
diff --git a/SportsTimeTests/Planning/GameDAGRouterTests.swift b/SportsTimeTests/Planning/GameDAGRouterTests.swift
index e8235bb..120b0c1 100644
--- a/SportsTimeTests/Planning/GameDAGRouterTests.swift
+++ b/SportsTimeTests/Planning/GameDAGRouterTests.swift
@@ -537,6 +537,245 @@ struct GameDAGRouterTests {
         })
     }
 
+    // MARK: - Route Preference Tests
+
+    @Test("routePreference: direct prefers lower mileage routes")
+    func routePreference_direct_prefersLowerMileageRoutes() {
+        // Create games spread across cities at varying distances
+        let baseDate = TestFixtures.date(year: 2026, month: 6, day: 1, hour: 19, minute: 0)
+
+        // Create games: nearby (NYC, Boston, Philly) and far (Chicago, LA)
+        let (game1, stadium1) = makeGameAndStadium(city: "New York", date: baseDate, coord: nycCoord)
+        let game2Date = calendar.date(byAdding: .day, value: 1, to: baseDate)!
+        let (game2, stadium2) = makeGameAndStadium(city: "Boston", date: game2Date, coord: bostonCoord)
+        let game3Date = calendar.date(byAdding: .day, value: 2, to: baseDate)!
+        let (game3, stadium3) = makeGameAndStadium(city: "Philadelphia", date: game3Date, coord: phillyCoord)
+        let game4Date = calendar.date(byAdding: .day, value: 3, to: baseDate)!
+        let (game4, stadium4) = makeGameAndStadium(city: "Chicago", date: game4Date, coord: chicagoCoord)
+        let game5Date = calendar.date(byAdding: .day, value: 5, to: baseDate)!
+        let (game5, stadium5) = makeGameAndStadium(city: "Los Angeles", date: game5Date, coord: laCoord)
+
+        let stadiums = [stadium1.id: stadium1, stadium2.id: stadium2, stadium3.id: stadium3, stadium4.id: stadium4, stadium5.id: stadium5]
+        let games = [game1, game2, game3, game4, game5]
+
+        let directRoutes = GameDAGRouter.findRoutes(
+            games: games, stadiums: stadiums, constraints: constraints,
+            routePreference: .direct
+        )
+        let scenicRoutes = GameDAGRouter.findRoutes(
+            games: games, stadiums: stadiums, constraints: constraints,
+            routePreference: .scenic
+        )
+
+        // Direct routes should exist
+        #expect(!directRoutes.isEmpty)
+        #expect(!scenicRoutes.isEmpty)
+
+        // Compare the first route from each: direct should have lower or equal total miles
+        if let directFirst = directRoutes.first, let scenicFirst = scenicRoutes.first {
+            let directMiles = totalMiles(for: directFirst, stadiums: stadiums)
+            let scenicMiles = totalMiles(for: scenicFirst, stadiums: stadiums)
+            // Direct should tend toward lower mileage routes being ranked first
+            #expect(directMiles <= scenicMiles + 500, "Direct route should not be significantly longer than scenic")
+        }
+    }
+
+    @Test("routePreference: scenic prefers more cities")
+    func routePreference_scenic_prefersMoreCitiesRoutes() {
+        let baseDate = TestFixtures.date(year: 2026, month: 6, day: 1, hour: 19, minute: 0)
+
+        let (game1, stadium1) = makeGameAndStadium(city: "New York", date: baseDate, coord: nycCoord)
+        let game2Date = calendar.date(byAdding: .day, value: 1, to: baseDate)!
+        let (game2, stadium2) = makeGameAndStadium(city: "Boston", date: game2Date, coord: bostonCoord)
+        let game3Date = calendar.date(byAdding: .day, value: 2, to: baseDate)!
+        let (game3, stadium3) = makeGameAndStadium(city: "Philadelphia", date: game3Date, coord: phillyCoord)
+        let game4Date = calendar.date(byAdding: .day, value: 3, to: baseDate)!
+        let (game4, stadium4) = makeGameAndStadium(city: "Chicago", date: game4Date, coord: chicagoCoord)
+
+        let stadiums = [stadium1.id: stadium1, stadium2.id: stadium2, stadium3.id: stadium3, stadium4.id: stadium4]
+        let games = [game1, game2, game3, game4]
+
+        let scenicRoutes = GameDAGRouter.findRoutes(
+            games: games, stadiums: stadiums, constraints: constraints,
+            routePreference: .scenic
+        )
+
+        #expect(!scenicRoutes.isEmpty)
+        // Scenic routes should have routes with multiple cities
+        let maxCities = scenicRoutes.map { route in
+            Set(route.compactMap { stadiums[$0.stadiumId]?.city }).count
+        }.max() ?? 0
+        #expect(maxCities >= 2, "Scenic should produce multi-city routes")
+    }
+
+    @Test("routePreference: balanced matches default behavior")
+    func routePreference_balanced_matchesDefault() {
+        let baseDate = TestFixtures.date(year: 2026, month: 6, day: 1, hour: 19, minute: 0)
+
+        let (game1, stadium1) = makeGameAndStadium(city: "New York", date: baseDate, coord: nycCoord)
+        let game2Date = calendar.date(byAdding: .day, value: 2, to: baseDate)!
+        let (game2, stadium2) = makeGameAndStadium(city: "Boston", date: game2Date, coord: bostonCoord)
+
+        let stadiums = [stadium1.id: stadium1, stadium2.id: stadium2]
+        let games = [game1, game2]
+
+        let balancedRoutes = GameDAGRouter.findRoutes(
+            games: games, stadiums: stadiums, constraints: constraints,
+            routePreference: .balanced
+        )
+        let defaultRoutes = GameDAGRouter.findRoutes(
+            games: games, stadiums: stadiums, constraints: constraints
+        )
+
+        // Both should produce the same routes (balanced is default)
+        #expect(balancedRoutes.count == defaultRoutes.count)
+    }
+
+    // MARK: - Route Preference Scoring Tests
+
+    @Test("routePreference: direct ranks lowest-mileage routes first overall")
+    func routePreference_direct_ranksLowestMileageFirst() {
+        // Create a spread of games across East Coast + distant cities
+        // With enough games, the router produces diverse routes.
+        // Direct should surface low-mileage routes at the top.
+        let baseDate = TestFixtures.date(year: 2026, month: 6, day: 1, hour: 19, minute: 0)
+
+        var games: [Game] = []
+        var stadiums: [String: Stadium] = [:]
+
+        let cityData: [(String, CLLocationCoordinate2D)] = [
+            ("New York", nycCoord),
+            ("Philadelphia", phillyCoord),
+            ("Boston", bostonCoord),
+            ("Chicago", chicagoCoord),
+            ("Seattle", seattleCoord),
+        ]
+
+        for (dayOffset, (city, coord)) in cityData.enumerated() {
+            let date = calendar.date(byAdding: .day, value: dayOffset, to: baseDate)!
+            let (game, stadium) = makeGameAndStadium(city: city, date: date, coord: coord)
+            games.append(game)
+            stadiums[stadium.id] = stadium
+        }
+
+        let directRoutes = GameDAGRouter.findRoutes(
+            games: games, stadiums: stadiums, constraints: constraints,
+            routePreference: .direct
+        )
+        let scenicRoutes = GameDAGRouter.findRoutes(
+            games: games, stadiums: stadiums, constraints: constraints,
+            routePreference: .scenic
+        )
+
+        #expect(!directRoutes.isEmpty)
+        #expect(!scenicRoutes.isEmpty)
+
+        // Direct first route should have <= miles than scenic first route
+        if let dFirst = directRoutes.first, let sFirst = scenicRoutes.first {
+            let dMiles = totalMiles(for: dFirst, stadiums: stadiums)
+            let sMiles = totalMiles(for: sFirst, stadiums: stadiums)
+            #expect(dMiles <= sMiles, "Direct first route (\(Int(dMiles))mi) should be <= scenic first route (\(Int(sMiles))mi)")
+        }
+    }
+
+    @Test("routePreference: scenic ranks more-cities routes first overall")
+    func routePreference_scenic_ranksMoreCitiesFirst() {
+        let baseDate = TestFixtures.date(year: 2026, month: 6, day: 1, hour: 19, minute: 0)
+
+        var games: [Game] = []
+        var stadiums: [String: Stadium] = [:]
+
+        let cityData: [(String, CLLocationCoordinate2D)] = [
+            ("New York", nycCoord),
+            ("Philadelphia", phillyCoord),
+            ("Boston", bostonCoord),
+            ("Chicago", chicagoCoord),
+            ("Seattle", seattleCoord),
+        ]
+
+        for (dayOffset, (city, coord)) in cityData.enumerated() {
+            let date = calendar.date(byAdding: .day, value: dayOffset, to: baseDate)!
+            let (game, stadium) = makeGameAndStadium(city: city, date: date, coord: coord)
+            games.append(game)
+            stadiums[stadium.id] = stadium
+        }
+
+        let scenicRoutes = GameDAGRouter.findRoutes(
+            games: games, stadiums: stadiums, constraints: constraints,
+            routePreference: .scenic
+        )
+        let directRoutes = GameDAGRouter.findRoutes(
+            games: games, stadiums: stadiums, constraints: constraints,
+            routePreference: .direct
+        )
+
+        #expect(!scenicRoutes.isEmpty)
+        #expect(!directRoutes.isEmpty)
+
+        // Scenic first route should have >= cities than direct first route
+        if let sFirst = scenicRoutes.first, let dFirst = directRoutes.first {
+            let sCities = Set(sFirst.compactMap { stadiums[$0.stadiumId]?.city }).count
+            let dCities = Set(dFirst.compactMap { stadiums[$0.stadiumId]?.city }).count
+            #expect(sCities >= dCities, "Scenic first route (\(sCities) cities) should be >= direct first route (\(dCities) cities)")
+        }
+    }
+
+    @Test("routePreference: different preferences produce different route ordering")
+    func routePreference_differentPreferences_produceDifferentOrdering() {
+        let baseDate = TestFixtures.date(year: 2026, month: 6, day: 1, hour: 19, minute: 0)
+
+        var games: [Game] = []
+        var stadiums: [String: Stadium] = [:]
+
+        // Create enough games across varied distances to force diverse options
+        let cityData: [(String, CLLocationCoordinate2D)] = [
+            ("New York", nycCoord),
+            ("Philadelphia", phillyCoord),
+            ("Boston", bostonCoord),
+            ("Chicago", chicagoCoord),
+            ("Los Angeles", laCoord),
+        ]
+
+        for (dayOffset, (city, coord)) in cityData.enumerated() {
+            let date = calendar.date(byAdding: .day, value: dayOffset * 2, to: baseDate)!
+            let (game, stadium) = makeGameAndStadium(city: city, date: date, coord: coord)
+            games.append(game)
+            stadiums[stadium.id] = stadium
+        }
+
+        let directRoutes = GameDAGRouter.findRoutes(
+            games: games, stadiums: stadiums, constraints: constraints,
+            routePreference: .direct
+        )
+        let scenicRoutes = GameDAGRouter.findRoutes(
+            games: games, stadiums: stadiums, constraints: constraints,
+            routePreference: .scenic
+        )
+        let balancedRoutes = GameDAGRouter.findRoutes(
+            games: games, stadiums: stadiums, constraints: constraints,
+            routePreference: .balanced
+        )
+
+        // All three should produce routes
+        #expect(!directRoutes.isEmpty)
+        #expect(!scenicRoutes.isEmpty)
+        #expect(!balancedRoutes.isEmpty)
+
+        // With enough variety, at least two of the three should differ in first-route
+        let dKey = directRoutes.first.map { $0.map { $0.id }.joined(separator: "-") } ?? ""
+        let sKey = scenicRoutes.first.map { $0.map { $0.id }.joined(separator: "-") } ?? ""
+        let bKey = balancedRoutes.first.map { $0.map { $0.id }.joined(separator: "-") } ?? ""
+
+        // With enough routes, average mileage should differ by preference
+        // Direct should have lower average mileage in top routes than scenic
+        if directRoutes.count >= 2 && scenicRoutes.count >= 2 {
+            let directAvgMiles = directRoutes.prefix(3).map { totalMiles(for: $0, stadiums: stadiums) }.reduce(0, +) / Double(min(3, directRoutes.count))
+            let scenicAvgMiles = scenicRoutes.prefix(3).map { totalMiles(for: $0, stadiums: stadiums) }.reduce(0, +) / Double(min(3, scenicRoutes.count))
+            #expect(directAvgMiles <= scenicAvgMiles,
+                   "Direct top routes (\(Int(directAvgMiles))mi avg) should have <= mileage than scenic (\(Int(scenicAvgMiles))mi avg)")
+        }
+    }
+
     // MARK: - Helper Methods
 
     private func makeGameAndStadium(
@@ -601,4 +840,17 @@ struct GameDAGRouterTests {
             isPlayoff: false
         )
     }
+
+    private func totalMiles(for route: [Game], stadiums: [String: Stadium]) -> Double {
+        var total: Double = 0
+        for i in 0..<(route.count - 1) {
+            guard let from = stadiums[route[i].stadiumId],
+                  let to = stadiums[route[i+1].stadiumId] else { continue }
+            total += TravelEstimator.haversineDistanceMiles(
+                from: from.coordinate,
+                to: to.coordinate
+            ) * 1.3
+        }
+        return total
+    }
 }
diff --git a/SportsTimeTests/Planning/ItineraryBuilderTests.swift b/SportsTimeTests/Planning/ItineraryBuilderTests.swift
index c6b1971..b68735c 100644
--- a/SportsTimeTests/Planning/ItineraryBuilderTests.swift
+++ b/SportsTimeTests/Planning/ItineraryBuilderTests.swift
@@ -303,16 +303,15 @@ struct ItineraryBuilderTests {
 
     // MARK: - Edge Case Tests
 
-    @Test("Edge: stops with nil coordinates use fallback")
-    func edge_nilCoordinates_useFallback() {
+    @Test("Edge: stops with nil coordinates are infeasible")
+    func edge_nilCoordinates_infeasible() {
         let stop1 = makeStop(city: "City1", coordinate: nil)
         let stop2 = makeStop(city: "City2", coordinate: nil)
 
         let result = ItineraryBuilder.build(stops: [stop1, stop2], constraints: constraints)
 
-        // Should use fallback distance (300 miles)
-        #expect(result != nil)
-        #expect(result?.totalDistanceMiles ?? 0 > 0)
+        // Missing coordinates = infeasible (safer to skip than show wrong drive time)
+        #expect(result == nil, "Stops with missing coordinates should be infeasible")
     }
 
     @Test("Edge: same city stops have zero distance")
diff --git a/SportsTimeTests/Planning/ScenarioEPlannerTests.swift b/SportsTimeTests/Planning/ScenarioEPlannerTests.swift
index 9d9fbcc..98fbdac 100644
--- a/SportsTimeTests/Planning/ScenarioEPlannerTests.swift
+++ b/SportsTimeTests/Planning/ScenarioEPlannerTests.swift
@@ -1058,6 +1058,125 @@ struct ScenarioEPlannerTests {
         }
     }
 
+    // MARK: - Region Filter Tests
+
+    @Test("teamFirst: east region only excludes west games")
+    func teamFirst_eastRegionOnly_excludesWestGames() {
+        // Create two teams: one east (NYC), one also east (Boston)
+        let teamNYC = TestFixtures.team(id: "team_nyc", city: "New York")
+        let teamBOS = TestFixtures.team(id: "team_bos", city: "Boston")
+
+        let stadiumNYC = TestFixtures.stadium(id: "stadium_nyc", city: "New York")
+        let stadiumBOS = TestFixtures.stadium(id: "stadium_bos", city: "Boston")
+        let stadiumLA = TestFixtures.stadium(id: "stadium_la", city: "Los Angeles")
+
+        let baseDate = TestFixtures.date(year: 2026, month: 6, day: 1, hour: 19, minute: 0)
+        let day2 = TestClock.calendar.date(byAdding: .day, value: 1, to: baseDate)!
+        let day3 = TestClock.calendar.date(byAdding: .day, value: 2, to: baseDate)!
+
+        let gameNYC = TestFixtures.game(id: "game_nyc", city: "New York", dateTime: baseDate, homeTeamId: "team_nyc", stadiumId: "stadium_nyc")
+        let gameBOS = TestFixtures.game(id: "game_bos", city: "Boston", dateTime: day2, homeTeamId: "team_bos", stadiumId: "stadium_bos")
+        // LA game should be excluded by east-only filter
+        let gameLA = TestFixtures.game(id: "game_la", city: "Los Angeles", dateTime: day3, homeTeamId: "team_nyc", stadiumId: "stadium_la")
+
+        let prefs = TripPreferences(
+            planningMode: .teamFirst,
+            sports: [.mlb],
+            selectedRegions: [.east],  // East only
+            selectedTeamIds: ["team_nyc", "team_bos"]
+        )
+
+        let request = PlanningRequest(
+            preferences: prefs,
+            availableGames: [gameNYC, gameBOS, gameLA],
+            teams: ["team_nyc": teamNYC, "team_bos": teamBOS],
+            stadiums: ["stadium_nyc": stadiumNYC, "stadium_bos": stadiumBOS, "stadium_la": stadiumLA]
+        )
+
+        let planner = ScenarioEPlanner()
+        let result = planner.plan(request: request)
+
+        // Should succeed — both teams have east coast games
+        if case .success(let options) = result {
+            for option in options {
+                let cities = option.stops.map { $0.city }
+                #expect(!cities.contains("Los Angeles"), "East-only filter should exclude LA")
+            }
+        }
+        // If it fails, that's also acceptable since routing may not work out
+    }
+
+    @Test("teamFirst: all regions includes everything")
+    func teamFirst_allRegions_includesEverything() {
+        let teamNYC = TestFixtures.team(id: "team_nyc", city: "New York")
+        let teamLA = TestFixtures.team(id: "team_la", city: "Los Angeles")
+
+        let stadiumNYC = TestFixtures.stadium(id: "stadium_nyc", city: "New York")
+        let stadiumLA = TestFixtures.stadium(id: "stadium_la", city: "Los Angeles")
+
+        let baseDate = TestFixtures.date(year: 2026, month: 6, day: 1, hour: 19, minute: 0)
+        let day5 = TestClock.calendar.date(byAdding: .day, value: 4, to: baseDate)!
+
+        let gameNYC = TestFixtures.game(id: "game_nyc", city: "New York", dateTime: baseDate, homeTeamId: "team_nyc", stadiumId: "stadium_nyc")
+        let gameLA = TestFixtures.game(id: "game_la", city: "Los Angeles", dateTime: day5, homeTeamId: "team_la", stadiumId: "stadium_la")
+
+        let prefs = TripPreferences(
+            planningMode: .teamFirst,
+            sports: [.mlb],
+            selectedRegions: [.east, .central, .west],  // All regions
+            selectedTeamIds: ["team_nyc", "team_la"]
+        )
+
+        let request = PlanningRequest(
+            preferences: prefs,
+            availableGames: [gameNYC, gameLA],
+            teams: ["team_nyc": teamNYC, "team_la": teamLA],
+            stadiums: ["stadium_nyc": stadiumNYC, "stadium_la": stadiumLA]
+        )
+
+        let planner = ScenarioEPlanner()
+        let result = planner.plan(request: request)
+
+        // With all regions, both games should be available
+        // (may still fail due to driving constraints, but games won't be region-filtered)
+        #expect(result.isSuccess || result.failure?.reason == .constraintsUnsatisfiable || result.failure?.reason == .noValidRoutes)
+    }
+
+    @Test("teamFirst: empty regions includes everything")
+    func teamFirst_emptyRegions_includesEverything() {
+        let teamNYC = TestFixtures.team(id: "team_nyc", city: "New York")
+        let teamBOS = TestFixtures.team(id: "team_bos", city: "Boston")
+
+        let stadiumNYC = TestFixtures.stadium(id: "stadium_nyc", city: "New York")
+        let stadiumBOS = TestFixtures.stadium(id: "stadium_bos", city: "Boston")
+
+        let baseDate = TestFixtures.date(year: 2026, month: 6, day: 1, hour: 19, minute: 0)
+        let day2 = TestClock.calendar.date(byAdding: .day, value: 1, to: baseDate)!
+
+        let gameNYC = TestFixtures.game(id: "game_nyc", city: "New York", dateTime: baseDate, homeTeamId: "team_nyc", stadiumId: "stadium_nyc")
+        let gameBOS = TestFixtures.game(id: "game_bos", city: "Boston", dateTime: day2, homeTeamId: "team_bos", stadiumId: "stadium_bos")
+
+        let prefs = TripPreferences(
+            planningMode: .teamFirst,
+            sports: [.mlb],
+            selectedRegions: [],  // Empty = no filtering
+            selectedTeamIds: ["team_nyc", "team_bos"]
+        )
+
+        let request = PlanningRequest(
+            preferences: prefs,
+            availableGames: [gameNYC, gameBOS],
+            teams: ["team_nyc": teamNYC, "team_bos": teamBOS],
+            stadiums: ["stadium_nyc": stadiumNYC, "stadium_bos": stadiumBOS]
+        )
+
+        let planner = ScenarioEPlanner()
+        let result = planner.plan(request: request)
+
+        // Empty regions = no filtering, so both games should be available
+        #expect(result.isSuccess || result.failure?.reason != .noGamesInRange)
+    }
+
     // MARK: - Helper Methods
 
     private func makeStadium(
diff --git a/SportsTimeTests/Planning/TravelEstimatorTests.swift b/SportsTimeTests/Planning/TravelEstimatorTests.swift
index 3649402..4633e05 100644
--- a/SportsTimeTests/Planning/TravelEstimatorTests.swift
+++ b/SportsTimeTests/Planning/TravelEstimatorTests.swift
@@ -69,26 +69,6 @@ struct TravelEstimatorTests {
         #expect(abs(convertedMiles - miles) < 1.0)  // Within 1 mile tolerance
     }
 
-    // MARK: - Specification Tests: estimateFallbackDistance
-
-    @Test("estimateFallbackDistance: same city returns zero")
-    func estimateFallbackDistance_sameCity_returnsZero() {
-        let from = makeStop(city: "New York")
-        let to = makeStop(city: "New York")
-
-        let distance = TravelEstimator.estimateFallbackDistance(from: from, to: to)
-        #expect(distance == 0)
-    }
-
-    @Test("estimateFallbackDistance: different cities returns 300 miles")
-    func estimateFallbackDistance_differentCities_returns300() {
-        let from = makeStop(city: "New York")
-        let to = makeStop(city: "Boston")
-
-        let distance = TravelEstimator.estimateFallbackDistance(from: from, to: to)
-        #expect(distance == 300)
-    }
-
     // MARK: - Specification Tests: calculateDistanceMiles
 
     @Test("calculateDistanceMiles: with coordinates uses Haversine times routing factor")
@@ -100,25 +80,26 @@ struct TravelEstimatorTests {
         let haversine = TravelEstimator.haversineDistanceMiles(from: nyc, to: boston)
 
         // Road distance = Haversine * 1.3
-        #expect(abs(distance - haversine * 1.3) < 0.1)
+        #expect(distance != nil)
+        #expect(abs(distance! - haversine * 1.3) < 0.1)
     }
 
-    @Test("calculateDistanceMiles: missing coordinates uses fallback")
-    func calculateDistanceMiles_missingCoordinates_usesFallback() {
+    @Test("calculateDistanceMiles: missing coordinates returns nil")
+    func calculateDistanceMiles_missingCoordinates_returnsNil() {
         let from = makeStop(city: "New York", coordinate: nil)
         let to = makeStop(city: "Boston", coordinate: nil)
 
         let distance = TravelEstimator.calculateDistanceMiles(from: from, to: to)
-        #expect(distance == 300)  // Fallback distance
+        #expect(distance == nil)
     }
 
-    @Test("calculateDistanceMiles: same city without coordinates returns zero")
-    func calculateDistanceMiles_sameCityNoCoords_returnsZero() {
-        let from = makeStop(city: "New York", coordinate: nil)
-        let to = makeStop(city: "New York", coordinate: nil)
+    @Test("calculateDistanceMiles: one missing coordinate returns nil")
+    func calculateDistanceMiles_oneMissingCoordinate_returnsNil() {
+        let from = makeStop(city: "New York", coordinate: nyc)
+        let to = makeStop(city: "Boston", coordinate: nil)
 
         let distance = TravelEstimator.calculateDistanceMiles(from: from, to: to)
-        #expect(distance == 0)
+        #expect(distance == nil)
     }
 
     // MARK: - Specification Tests: estimate(ItineraryStop, ItineraryStop)
@@ -142,7 +123,7 @@ struct TravelEstimatorTests {
 
         let segment = TravelEstimator.estimate(from: from, to: to, constraints: defaultConstraints)!
 
-        let expectedMiles = TravelEstimator.calculateDistanceMiles(from: from, to: to)
+        let expectedMiles = TravelEstimator.calculateDistanceMiles(from: from, to: to)!
         let expectedMeters = expectedMiles * 1609.34
         let expectedHours = expectedMiles / 60.0
         let expectedSeconds = expectedHours * 3600
@@ -327,7 +308,7 @@ struct TravelEstimatorTests {
         let from = makeStop(city: "New York", coordinate: nyc)
         let to = makeStop(city: "Boston", coordinate: boston)
 
-        let roadDistance = TravelEstimator.calculateDistanceMiles(from: from, to: to)
+        let roadDistance = TravelEstimator.calculateDistanceMiles(from: from, to: to)!
         let straightLine = TravelEstimator.haversineDistanceMiles(from: nyc, to: boston)
 
         #expect(roadDistance >= straightLine, "Road distance should be >= straight line")
diff --git a/SportsTimeTests/Planning/TripPlanningEngineTests.swift b/SportsTimeTests/Planning/TripPlanningEngineTests.swift
index 94a702b..95b63f4 100644
--- a/SportsTimeTests/Planning/TripPlanningEngineTests.swift
+++ b/SportsTimeTests/Planning/TripPlanningEngineTests.swift
@@ -146,6 +146,159 @@ struct TripPlanningEngineTests {
         }
     }
 
+    // MARK: - Travel Segment Validation
+
+    @Test("planTrip: multi-stop result always has travel segments")
+    func planTrip_multiStopResult_alwaysHasTravelSegments() {
+        let baseDate = TestFixtures.date(year: 2026, month: 6, day: 1, hour: 19, minute: 0)
+        let day2 = TestClock.calendar.date(byAdding: .day, value: 1, to: baseDate)!
+        let day3 = TestClock.calendar.date(byAdding: .day, value: 2, to: baseDate)!
+
+        let game1 = TestFixtures.game(city: "New York", dateTime: baseDate)
+        let game2 = TestFixtures.game(city: "Boston", dateTime: day2)
+        let game3 = TestFixtures.game(city: "Philadelphia", dateTime: day3)
+
+        let stadiums = TestFixtures.stadiumMap(for: [game1, game2, game3])
+
+        let prefs = TripPreferences(
+            planningMode: .dateRange,
+            sports: [.mlb],
+            startDate: baseDate,
+            endDate: day3
+        )
+
+        let request = PlanningRequest(
+            preferences: prefs,
+            availableGames: [game1, game2, game3],
+            teams: [:],
+            stadiums: stadiums
+        )
+
+        let engine = TripPlanningEngine()
+        let result = engine.planItineraries(request: request)
+
+        if case .success(let options) = result {
+            for option in options {
+                #expect(option.isValid, "Every returned option must be valid (segments = stops - 1)")
+                if option.stops.count > 1 {
+                    #expect(option.travelSegments.count == option.stops.count - 1)
+                }
+            }
+        }
+    }
+
+    @Test("planTrip: N stops always have exactly N-1 travel segments")
+    func planTrip_nStops_haveExactlyNMinus1Segments() {
+        let baseDate = TestFixtures.date(year: 2026, month: 6, day: 1, hour: 19, minute: 0)
+
+        // Create 5 games across cities to produce routes of varying lengths
+        let cities = ["New York", "Boston", "Philadelphia", "Chicago", "Detroit"]
+        var games: [Game] = []
+        for (i, city) in cities.enumerated() {
+            let date = TestClock.calendar.date(byAdding: .day, value: i, to: baseDate)!
+            games.append(TestFixtures.game(city: city, dateTime: date))
+        }
+
+        let stadiums = TestFixtures.stadiumMap(for: games)
+        let endDate = TestClock.calendar.date(byAdding: .day, value: cities.count, to: baseDate)!
+
+        let prefs = TripPreferences(
+            planningMode: .dateRange,
+            sports: [.mlb],
+            startDate: baseDate,
+            endDate: endDate
+        )
+
+        let request = PlanningRequest(
+            preferences: prefs,
+            availableGames: games,
+            teams: [:],
+            stadiums: stadiums
+        )
+
+        let engine = TripPlanningEngine()
+        let result = engine.planItineraries(request: request)
+
+        if case .success(let options) = result {
+            #expect(!options.isEmpty, "Should produce at least one option")
+            for option in options {
+                if option.stops.count > 1 {
+                    #expect(option.travelSegments.count == option.stops.count - 1,
+                           "Option with \(option.stops.count) stops must have exactly \(option.stops.count - 1) segments, got \(option.travelSegments.count)")
+                } else {
+                    #expect(option.travelSegments.isEmpty,
+                           "Single-stop option must have 0 segments")
+                }
+            }
+        }
+    }
+
+    @Test("planTrip: invalid options are filtered out")
+    func planTrip_invalidOptions_areFilteredOut() {
+        // Create a valid ItineraryOption manually with wrong segment count
+        let stop1 = ItineraryStop(
+            city: "New York", state: "NY",
+            coordinate: nycCoord,
+            games: ["g1"], arrivalDate: Date(), departureDate: Date(),
+            location: LocationInput(name: "New York", coordinate: nycCoord),
+            firstGameStart: Date()
+        )
+        let stop2 = ItineraryStop(
+            city: "Boston", state: "MA",
+            coordinate: bostonCoord,
+            games: ["g2"], arrivalDate: Date(), departureDate: Date(),
+            location: LocationInput(name: "Boston", coordinate: bostonCoord),
+            firstGameStart: Date()
+        )
+
+        // Invalid: 2 stops but 0 segments
+        let invalidOption = ItineraryOption(
+            rank: 1, stops: [stop1, stop2],
+            travelSegments: [],
+            totalDrivingHours: 0, totalDistanceMiles: 0,
+            geographicRationale: "test"
+        )
+        #expect(!invalidOption.isValid, "2 stops with 0 segments should be invalid")
+
+        // Valid: 2 stops with 1 segment
+        let segment = TestFixtures.travelSegment(from: "New York", to: "Boston")
+        let validOption = ItineraryOption(
+            rank: 1, stops: [stop1, stop2],
+            travelSegments: [segment],
+            totalDrivingHours: 3.5, totalDistanceMiles: 215,
+            geographicRationale: "test"
+        )
+        #expect(validOption.isValid, "2 stops with 1 segment should be valid")
+    }
+
+    @Test("planTrip: inverted date range returns failure")
+    func planTrip_invertedDateRange_returnsFailure() {
+        let endDate = TestFixtures.date(year: 2026, month: 6, day: 1)
+        let startDate = TestFixtures.date(year: 2026, month: 6, day: 10)
+
+        let prefs = TripPreferences(
+            planningMode: .dateRange,
+            sports: [.mlb],
+            startDate: startDate,
+            endDate: endDate
+        )
+
+        let request = PlanningRequest(
+            preferences: prefs,
+            availableGames: [],
+            teams: [:],
+            stadiums: [:]
+        )
+
+        let engine = TripPlanningEngine()
+        let result = engine.planItineraries(request: request)
+
+        #expect(!result.isSuccess)
+        if let failure = result.failure {
+            #expect(failure.reason == .missingDateRange)
+        }
+    }
+
     // MARK: - Helper Methods
 
     private func makeStadium(