Sidetrip offers three ways to create a trip: on-device AI generation, JSON import, and the external AI prompt workflow. This guide explains each method in detail.
Overview: Three Ways to Create a Trip
| Method | Best For | Requirements |
|---|---|---|
| Generate with AI | Quick full itineraries from a description | Sidetrip Pro + iOS 26 / macOS 26 with Apple Intelligence |
| Import from JSON | Bringing in trips created externally or shared as files | A valid Sidetrip JSON file |
| Copy Prompt (external AI) | Using ChatGPT, Claude, or another AI to generate a JSON file | An external AI assistant (web, app, or API) |
Generate with AI
Requires Sidetrip Pro and a device running iOS 26 / macOS 26 with Apple Intelligence support.
AI generation creates a complete trip itinerary — parts, days, stops, accommodations, and transportation — directly on your device using Apple Intelligence. No trip data is sent to any external server.
How to Generate a Trip
- Tap the + button on the trips list
- Select Generate with AI
- Describe your trip in the text field. Include details like:
- Destination(s) and origin
- Travel dates or number of days
- Travel style (relaxed, packed, family-friendly, etc.)
- Interests or must-see places
- Tap Generate to start
- Watch the progress as Sidetrip works through five generation phases: trip skeleton, transportation, accommodations, daily stops, and final assembly
- When complete, the new trip appears in your trips list
Generation Phases
Sidetrip's AI generation works in five sequential phases to stay within the on-device model's context limits:
| Phase | What Gets Built |
|---|---|
| 1 — Trip Skeleton | Title, tagline, parts, day titles and summaries |
| 2 — Transportation | Flights, trains, ferries, and other transit segments |
| 3 — Accommodations | Hotels and lodging with check-in/check-out dates |
| 4 — Daily Stops | Individual stops, times, and tips for each day (one pass per day) |
| 5 — Assembly | Combining all phases into the final trip and saving to your library |
Tips for Better Results
- Be specific about dates or duration: "10 days in Japan, mid-April" generates better results than "a trip to Japan"
- Mention pacing preferences: "leisurely pace with afternoons free" or "as many sites as possible"
- List any fixed points: "must include a day trip to Nara" or "flying into Tokyo, out of Osaka"
- Specify travel group: "two adults and a 5-year-old" helps the AI pick appropriate stops
What if Generation Fails?
If generation is interrupted or fails partway through, you'll see an error message with the option to try again. On-device AI can occasionally time out on longer trips — try a shorter description or fewer days if you encounter repeated failures.
Import from JSON
You can import any trip file in Sidetrip's JSON format. This is useful for:
- Trips generated externally using the Copy Prompt workflow
- Trip files shared as attachments by another Sidetrip user
- Updating an existing trip with a revised version of the same file
How to Import a Trip
- Tap the + button on the trips list
- Select Import JSON
- Choose your import method:
- Paste JSON: Paste the JSON text directly into the text field
- Open File: Use the file picker to select a
.jsonfile from Files, iCloud Drive, or another location
- Tap Import
- The trip appears in your list immediately if the file is valid
Updating an Existing Trip
If the JSON file contains a trip ID that matches an existing trip in your library, Sidetrip will ask whether you want to update the existing trip with the new data. Choosing Update is safe — it preserves all your existing visit statuses and notes for any stops whose IDs match between the old and new versions.
JSON Format
Sidetrip uses a JSON schema (v2.0) with the following top-level structure:
schema_version: Always"2.0"trip: The trip object containing title, tagline, dates, origin, destination, parts, accommodations, and transportations- Each part contains an array of days
- Each day contains an array of stops and references to accommodations by ID
Use the Copy Prompt workflow (described below) to get the full schema specification automatically included in a ready-to-use prompt.
You can also export any existing trip back to this same JSON format from the trip overview — see Exporting Trips in the Planning Your Trip article for details.
Copy Prompt (External AI Workflow)
If you don't have a device that supports Apple Intelligence, or if you prefer to use an external AI assistant, the Copy Prompt workflow lets you generate a compatible trip file using ChatGPT, Claude, Gemini, or any other AI.
How It Works
- Tap the + button on the trips list
- Select Copy Prompt
- The full Sidetrip JSON schema specification is copied to your clipboard, along with instructions for the AI and a placeholder for your trip description
- Open your preferred AI assistant (ChatGPT, Claude, etc.)
- Paste the prompt and fill in the trip details at the end (destination, duration, style, etc.)
- Send the prompt — the AI will respond with a complete Sidetrip-format JSON
- Copy the JSON response
- Return to Sidetrip, tap + → Import JSON → Paste JSON, paste the text, and import
Tips for the External Prompt
- Include as much detail as you want about your trip at the end of the prompt — the schema instructions are already in the prompt text
- If the AI truncates its response, ask it to continue or to regenerate a shorter trip (fewer days) first
- You can ask the AI to revise the JSON before importing — for example, to swap out a day's stops or adjust timings
Deleting a Trip
To delete a trip you no longer need:
- iPhone/iPad: Swipe left on the trip in the trips list and tap Delete
- Mac: Right-click the trip and select Delete
Warning: Deleting a trip is permanent and cannot be undone. If the trip is shared with others, they will lose access. Consider archiving a trip instead if you want to hide it without permanently removing it.