Creating Trips

Tap the + button on the trips list to open Create with AI. It offers two ways to create a trip: an external AI of your choice, or Apple Intelligence built into Sidetrip. You can also import any Sidetrip trip file from the same screen. This guide explains each method in detail.

Overview: Ways to Create a Trip

On the free tier, which includes one trip, tapping + when you already have a trip offers Sidetrip Pro instead.

Apple Intelligence

Requires a device running iOS 26 / macOS 26 or later with Apple Intelligence support. Generation access is unchanged for Free and Pro users within their existing trip limits.

AI generation creates a complete trip itinerary with parts, days, stops, accommodations, and transportation using Apple Intelligence. Generation remains local on iOS 26 / macOS 26. On iOS 27 / macOS 27 or later, it uses Apple Private Cloud Compute (PCC) exclusively, sending your prompt and required context to Apple's PCC servers for processing.

PCC requires internet access and is subject to Apple's daily usage quota, independent of Sidetrip Pro. Pro does not increase or remove that quota. Sidetrip shows connectivity, availability, and quota failures without silently switching to another model or processing location.

How to Generate a Trip

1. Tap the + button on the trips list
2. In the Apple Intelligence section, 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
3. Tap Generate Trip to start
4. Watch the progress as Sidetrip builds and saves your itinerary
5. When complete, the new trip appears in your trips list

If Apple Intelligence can't be used, the section explains why — for example, if it's turned off in Settings, its model is still downloading, or on OS 27+, Apple's daily Private Cloud Compute limit has been reached. When you're close to that limit, Sidetrip warns you before you generate.

Generation Phases

On iOS 26 / macOS 26, Sidetrip's local AI generation works in five sequential phases to stay within the on-device model's context limits, which should not be assumed to apply to PCC on OS 27+. The local phases are:

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 OS 27+, check your internet connection and any PCC availability or quota error. Wait for service to become available or the daily quota to reset before retrying; upgrading to Pro does not bypass Apple's quota. There is no silent local fallback. On OS 26, on-device AI can occasionally time out on longer trips — try a shorter description or fewer days if you encounter repeated failures.

Import a Trip File

You can import any trip file in Sidetrip's JSON format. This is useful for:

• Trips generated with an external AI
• Trips exported from Sidetrip as a backup or from another account
• 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

1. Tap the + button on the trips list
2. In the Generate with External AI section, choose:
   • Paste from Clipboard: Imports JSON text you've copied
   • Import Trip File: Opens the file picker to select a .json file from Files, iCloud Drive, or another location
3. The trip appears in your list immediately if the file is valid

If the Import Fails

If the JSON has a problem — a syntax error, a missing or invalid field, or a date that isn't in YYYY-MM-DD format — Sidetrip tells you what's wrong and where. Tap Copy for AI and paste the message into the AI chat that created the JSON so it can fix it, then import the corrected reply. A Markdown code fence (```json) around the JSON is removed automatically.

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 keeps the visit status of every stop whose ID matches between the old and new versions, as well as the 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.

You can also update a trip from inside it: in the trip overview, tap ⋯ → Update Trip, then Choose File or Paste from Clipboard. Sidetrip checks that the file is for the same trip before replacing anything. Updating a shared trip keeps it shared, and everyone with access sees the changes.

JSON Format

Sidetrip uses a JSON schema (v2.1) with the following top-level structure:

• version: The schema version, "2.1". Files from earlier versions ("2.0") still import.
• 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 Get Prompt (described below) to get the full schema specification in a ready-to-use prompt. Cover photos aren't part of the JSON format.

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.

Generate with External AI

If you don't have a device that supports Apple Intelligence, or if you prefer to use an external AI assistant, you can plan your trip with ChatGPT, Claude, Gemini, or any other AI and have it produce a compatible trip file.

How It Works

1. Plan your trip with your preferred AI assistant. Talk through the destination, dates, pace, and must-see places until you're happy with the plan
2. In Sidetrip, tap the + button on the trips list
3. Tap Get Prompt, then Copy. The prompt contains the full Sidetrip JSON schema and instructions for the AI
4. Paste the prompt into the same AI conversation and send it
5. When the AI responds with JSON, copy it — or save it as a .json file
6. Return to Sidetrip and tap Paste from Clipboard or Import Trip File

Tips for the External Prompt

• Do your planning first — the prompt asks the AI to turn the trip plan you just discussed into JSON, so the more you've agreed on, the better the result
• 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: Swipe left on the trip with two fingers on the trackpad and click Delete

Warning: Deleting a trip removes it from all your devices and iCloud, 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.