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. While a trip is in progress, an Up Next card shows your next stop with Start and Mark Visited buttons. 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.
AI trip generation on iOS 27 / macOS 27 or later requires internet access for Apple Private Cloud Compute (PCC). It does not fall back to local processing when offline. Generation on iOS 26 / macOS 26 remains on-device. The Pro-only assistant's On Device mode works offline; its Private Cloud mode on iOS 27 / macOS 27 or later requires internet access.
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 to open Create with AI. From there you can describe your trip and tap Generate Trip to use Apple Intelligence (on supported devices), or tap Get Prompt to plan it with ChatGPT, Claude, Gemini, or any other AI. Bring the AI's reply, or any Sidetrip trip file, into the app with Paste from Clipboard or Import Trip File.
Can I edit my trip after creating it?
Yes. The Pro-only 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. Without the assistant, you can:
- Add personal notes to any stop, accommodation, or transportation booking
- Add a cover photo to the trip or any day
- Mark all of a day's stops at once from the day's ⋯ menu
- Replace the trip with an edited JSON file from the trip overview's ⋯ menu → Update Trip
What is the visit status feature?
Each stop has a visit status that cycles through four states as you tap the circle next to it on the day's timeline:
- 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.
If you don't need In Progress, turn off Settings → Stops → Enable In Progress State and tapping a stop cycles between Not Visited, Visited, and Skipped.
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. Accommodations and transportation bookings have a Notes field too. Notes are saved immediately and sync via iCloud.
What stop categories are available?
Each stop is assigned one of five categories:
- Attraction: Sights, museums, landmarks
- Food: Restaurants, cafes, markets
- Scenic: Viewpoints, parks, nature
- Transport: Flights, buses, trains, airports, stations
- Stay: Check-in, waking up at, and returning to your accommodation
How do I archive a trip?
Swipe right on a trip in the trips list and tap Archive. Archived trips are hidden from the main list. To see them, open the Sort & Group menu in the toolbar and choose Show Archived Trips; swipe right on an archived trip to unarchive it. Archiving syncs across your own devices but is personal — it doesn't hide the trip for anyone you share it with.
Can I add a cover photo to a trip or a day?
Yes. Open the trip overview or a day, tap ⋯, and choose Add Cover (or Edit Cover). Pick a photo from your library or an image file. Covers are free, sync through iCloud, and are shared with everyone who has access to the trip. With Sidetrip Pro on iOS 27 / macOS 27 or later, you can also tap Generate with AI to create a cover with Image Playground.
Can Sidetrip open the trip I'm on automatically?
Yes. Turn on Settings → Trips → Open Current Trip at Launch. When one of your trips is happening today, Sidetrip opens it when you launch the app. With Open Today's Day also on (the default), it opens straight to today's day instead of the overview. Archived trips are skipped, and if several trips overlap, the one that started most recently opens.
Sidetrip Pro
What is included in Sidetrip Pro?
Sidetrip Pro unlocks:
- Creating more than one trip (the free tier includes one trip total)
- The AI assistant inside trips and day views
- Sharing your trips with others
- Accepting shared trips from others (when you already have one trip)
- The CarPlay app
- The Apple Watch companion for browsing trips and updating visit status
- AI-generated cover images (iOS 27 / macOS 27 or later)
- Alternate app icons (iPhone and iPad)
The free tier lets you create and use one trip with full itinerary viewing, stop tracking, notes, and cover photos. AI trip generation is available to both Free and Pro users on supported devices, within their existing trip limits.
How do I purchase Sidetrip Pro?
Open Settings (the gear button on the trips list on iPhone and iPad, or Sidetrip → Settings on Mac) and tap the Sidetrip Pro card. 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 Apple Intelligence:
- AI Trip Generation: Describe your trip in plain language and Sidetrip builds a complete itinerary including parts, days, stops, accommodations, and transportation. Generation runs locally on iOS 26 / macOS 26 and exclusively through Apple Private Cloud Compute on iOS 27 / macOS 27 or later.
- AI Assistant: A conversational assistant inside your trip or day view that can rename, update, and add content using natural language. It is Pro-only. On iOS 27 / macOS 27 or later you can choose On Device or Private Cloud, which can plan and edit your whole trip.
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?
On iOS 27 / macOS 27 or later, generation sends your prompt and required context to Apple's Private Cloud Compute servers. On iOS 26 / macOS 26, generation remains local. The assistant's On Device mode does not send data to servers for AI processing. Its Private Cloud mode, on iOS 27 / macOS 27 or later, sends your messages and the trip details it needs to Apple's Private Cloud Compute servers.
Does Sidetrip Pro remove Apple's daily generation quota?
No. PCC requires internet access and is subject to Apple's daily usage quota, independent of Sidetrip Pro. Pro does not increase or remove this quota. Generation access is unchanged for Free and Pro users within their trip limits. The Private Cloud assistant uses the same quota as generation; the On Device assistant does not use PCC or consume its quota. If PCC is unavailable, offline, or quota-limited, Sidetrip shows the issue without silently switching to a different model or processing location.
What if I don't have a compatible device for AI generation?
You can still create full itineraries using Generate with External AI. Plan your trip with any AI assistant (like ChatGPT, Claude, or Gemini), then tap Get Prompt and paste the prompt into the same conversation. The AI replies with a compatible JSON file, which you import with Paste from Clipboard or Import Trip File.
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, with Sidetrip Pro. Open the trip, tap Share Trip in the Sharing section of the trip overview, and invite people by their iCloud email address or send them a link. Anyone can accept a shared trip, within the free tier's one-trip limit. Shared trips stay in sync — when anyone with permission to edit updates the itinerary, everyone with access sees the changes.
Can the people I share with edit the trip?
Yes, if you allow it. When you invite someone, you choose whether they can make changes or only view the trip. People who can make changes can edit anything — stops, notes, visit statuses, and titles. People with view-only access can see everything but can't change anything.
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 Leave. 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 (v2.1) for trip data. The structure includes a trip with parts, days, stops, accommodations, and transportation. You can get the exact schema by tapping + and then Get Prompt — 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 keeps the visit status of every stop whose ID matches, along with your trip and day covers. Everything else, including notes, is replaced with what's in the file — so if you've added notes in the app, export the trip and edit that file rather than an older copy.
Can I export my trips?
Yes. From any trip's overview, tap the ⋯ button in the
toolbar, choose Export Trip, and then
Save as File (to export as a .json file) or
Copy to Clipboard (to copy the JSON text). Cover photos
aren't included in the file. The exported data uses the same Sidetrip JSON format (v2.1), 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. On earlier OS versions, the Apple Intelligence section doesn't appear. On iOS 26 / macOS 26 or later, it explains what's missing — for example, if Apple Intelligence is turned off or its model is still downloading. You can always use Generate with External AI instead.
On iOS 27 / macOS 27 or later, also check your internet connection and any PCC availability or daily quota error. Try again when the service is available or the quota resets; upgrading to Pro does not resolve Apple's quota limit.
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!