What is Sidetrip?
Sidetrip is a native Apple app for building and experiencing detailed travel itineraries. It organizes your trip into parts, days, and individual stops — each with times, descriptions, maps, and practical details like opening hours, cost, and website links. Your trips sync across all your Apple devices via iCloud, and you can share any trip with family or friends.
Which platforms does Sidetrip support?
Sidetrip runs on:
- iPhone/iPad: iOS/iPadOS 18.0 or later
- Mac: macOS 15.0 (Sequoia) or later
- Apple Watch: watchOS 11.0 or later with Sidetrip Pro
AI trip generation and the AI assistant require iOS 26 / macOS 26 or later on a device that supports Apple Intelligence.
What can I do with Sidetrip on Apple Watch?
The Sidetrip Pro Watch companion lets you browse active trips, parts, days, stops, accommodations, and transportation details. You can see day progress and update a stop's visit status when the trip is editable. Trip creation, JSON import/export, maps, navigation, sharing management, and AI features remain in the iPhone, iPad, and Mac app.
Does Sidetrip require an account?
No account is needed. Sidetrip uses your existing iCloud account for syncing your trips across devices. No separate sign-up is required.
Do I need an internet connection?
Sidetrip works offline. Your trips are stored on your device and sync via iCloud when a connection is available. You can view and edit your itinerary, update stop statuses, and add notes without internet access. On Apple Watch, downloaded trips remain available offline and changes sync when the connection returns.
Trips & Itineraries
How is a trip structured?
A trip is organized into three levels:
- Parts: Named segments of your trip (e.g., "Paris", "Lyon", "Day Trips"). Each part groups a set of consecutive days.
- Days: Individual calendar days, each with a title, summary, and list of stops.
- Stops: Individual activities or places within a day, with time, category, description, map pin, address, website, cost, and more.
A trip also includes a list of Accommodations and Transportation segments for quick reference while traveling.
How do I create a trip?
Tap the + button on the trips list. You can generate a trip using on-device AI (on supported devices), import a trip from a JSON file, or use the built-in prompt to generate a JSON file with any external AI assistant and then import it.
Can I edit my trip after creating it?
Yes. The AI assistant (available inside any trip or day view) lets you rename trips, update taglines, rename days and parts, update summaries, and manage stops — all using natural language. You can also add personal notes to any stop directly.
What is the visit status feature?
Each stop has a visit status that cycles through four states as you tap the status badge:
- Not Visited: The default state before you arrive
- In Progress: You're currently at this stop
- Visited: You've been here
- Skipped: You decided to skip this stop
The day view shows an overall progress indicator based on your stops' statuses. When you update a trip from a new import, your visit statuses are preserved.
Can I add personal notes to stops?
Yes. Open any stop's detail view and tap the Notes field to add or edit your own notes. Notes are saved immediately and sync via iCloud.
What stop categories are available?
Each stop is assigned one of four categories:
- Attraction: Sights, museums, landmarks
- Food: Restaurants, cafes, markets
- Scenic: Viewpoints, parks, nature
- Transport: Transit connections, airports, stations
How do I archive a trip?
Swipe left on a trip in the trips list and tap Archive. Archived trips are hidden from the main list by default. Tap the Show Archived toggle in the toolbar to reveal them. Archiving is local to your device — it does not affect iCloud sync or shared copies.
Sidetrip Pro
What is included in Sidetrip Pro?
Sidetrip Pro unlocks:
- Creating more than one trip (the free tier includes one trip total)
- AI trip generation
- The AI assistant inside trips and day views
- Accepting shared trips from others (when you already have one trip)
- The Apple Watch companion for browsing trips and updating visit status
The free tier lets you create and use one trip with full itinerary viewing, stop tracking, and notes.
How do I purchase Sidetrip Pro?
Go to Settings and tap Upgrade to Pro. Sidetrip Pro is available as a one-time purchase from the App Store.
How do I restore my purchase on a new device?
Go to Settings and tap Restore Purchases. Make sure you're signed in with the same Apple ID used for the original purchase.
Purchases and restores are completed on iPhone, iPad, or Mac. After Pro access syncs through iCloud, open the Watch app and tap Try Again if it still shows the locked screen.
AI Features
What AI features does Sidetrip include?
Sidetrip includes two AI features, both powered by on-device Apple Intelligence:
- AI Trip Generation: Describe your trip in plain language and Sidetrip builds a complete itinerary — including parts, days, stops, accommodations, and transportation — entirely on your device.
- AI Assistant: A conversational assistant inside your trip or day view that can rename, update, and add content using natural language.
Are AI features available on all devices?
AI features require iOS 26 / macOS 26 or later on a device that supports Apple Intelligence. On older devices or OS versions, AI features are not available but all other Sidetrip features work normally.
Is my trip data sent to Apple or any server for AI processing?
No. All AI processing in Sidetrip uses on-device Apple Intelligence. Your trip data never leaves your device for AI features.
What if I don't have a compatible device for AI generation?
You can still create full itineraries using the Copy Prompt option. This gives you a structured prompt to paste into any AI assistant (like ChatGPT, Claude, etc.) outside the app. The AI assistant of your choice generates a compatible JSON file, which you then import into Sidetrip.
Syncing & Sharing
How do trips sync across my devices?
Trips sync automatically via iCloud using CloudKit. Any changes you make on one device appear on your other devices shortly after. No manual sync is needed.
Can I share a trip with someone else?
Yes. Open any trip, tap the share icon in the toolbar, and invite people by their iCloud email address. Shared trips stay in sync — when the owner updates the itinerary, everyone with access sees the changes.
Can the people I share with edit the trip?
Shared trips are currently view-only for recipients. The trip owner is the only person who can make edits.
What happens if I leave a shared trip?
You can remove a shared trip from your Shared with Me list by swiping left on it and tapping Remove. The original trip in the owner's account is not affected.
Import & Export
What file format does Sidetrip use for import?
Sidetrip uses a JSON-based schema (v2.0) for trip data. The structure includes a trip with parts, days, stops, accommodations, and transportation. You can get the exact schema by tapping Copy Prompt when creating a trip — the prompt contains the full specification.
What happens if I import a trip that already exists?
Sidetrip detects duplicates by trip ID. If a matching trip is found, you'll be asked whether you want to update the existing trip with the new data. Updating preserves all your existing visit statuses and notes for any stops whose IDs match.
Can I export my trips?
Yes. From any trip's overview, tap the ⋯ button in the
toolbar and choose either Save as File (to export as a
.json file) or Copy to Clipboard (to copy the
JSON text). The exported data uses the same Sidetrip JSON format (v2.0), so
it can be imported on another device or shared with anyone.
Troubleshooting
My trips aren't syncing across devices
Make sure iCloud is enabled for Sidetrip on all your devices: go to Settings → [Your Name] → iCloud and check that Sidetrip is toggled on. Also ensure you're signed into the same iCloud account on all devices.
AI generation isn't available
AI features require iOS 26 / macOS 26 or later on a device that supports Apple Intelligence. If your device or OS version doesn't meet these requirements, the option will not appear. Use the Copy Prompt workflow instead.
How do I report a bug or request a feature?
Contact us through the support link in the app's Settings or reach out through our support channels. We appreciate your feedback!