The Sidetrip AI assistant lets you edit your trip using plain English. Open it inside any trip or day view and type what you'd like to change — the assistant will understand your request and make the edits for you.
Requirements
- Sidetrip Pro
- A device running iOS 26 / macOS 26 or later with Apple Intelligence support
All AI processing happens on your device using Apple Intelligence. Your trip data is never sent to any external server.
Opening the Assistant
The assistant button appears in the toolbar of the trip overview and individual day views:
- Trip-level assistant: Available from the trip overview toolbar. Use this to make changes that span the whole trip (rename the trip, update the tagline, rename a day, etc.)
- Day-level assistant: Available from any day's detail view toolbar. Use this to make changes specific to that day's stops (add a stop, change a time, update a description, etc.)
Tap the assistant icon to open the chat panel.
What the Assistant Can Do
Trip-Level Actions
When opened from the trip overview, the assistant can:
| Action | Example Request |
|---|---|
| Rename the trip | "Rename this trip to 'Summer in Andalusia'" |
| Update the trip tagline | "Change the tagline to 'Sun, tapas, and flamenco'" |
| Rename a day | "Rename Day 4 to 'Alhambra & Albaicín'" |
| Update a day's summary | "Update the summary for Day 2 to focus on the old town" |
| List all days | "Show me all the days in this trip" |
Day-Level Actions
When opened from a day view, the assistant can:
| Action | Example Request |
|---|---|
| List all stops | "What stops do we have today?" |
| Rename a stop | "Rename the market stop to 'La Boqueria'" |
| Update a stop's description | "Update the description for the cathedral to mention the rooftop views" |
| Change a stop's time | "Move the dinner reservation to 8:30 PM" |
| Add a new stop | "Add a coffee break at 10am at a local café" |
| Remove a stop | "Remove the shopping stop" |
Using the Assistant
Making a Request
- Tap the assistant icon in the toolbar to open the chat panel
- Type your request in the message field
- Tap Send
- The assistant responds with a confirmation of what it changed, or asks for clarification if needed
Conversation Context
The assistant remembers your conversation within a session. You can make follow-up requests without re-explaining context:
- "Add a stop for gelato after the museum"
- "Actually, make it a 30-minute stop"
- "And set the category to Food"
Reviewing Changes
Changes made by the assistant are applied directly to your trip and saved immediately. The updated trip syncs via iCloud to all your devices. You can see the changes reflected in the day view right away.
Session Limits
Each assistant session has a context window limit. If you make many requests in a single session, you may see a message that the session has reached its limit.
Starting a New Session
When the session is exhausted, tap New Session in the assistant panel. This clears the conversation history and starts a fresh session. All changes you made in the previous session are preserved in your trip — only the conversation context resets.
Tips for Best Results
- Be specific about which stop or day: "Rename the Louvre stop" works better than "rename the museum"
- One change at a time: The assistant handles each request accurately; very long compound requests may require clarification
- If the assistant asks for clarification: Provide the additional detail — for example, if there are two stops with similar names, specify which one you mean
- Use the right scope: Use the trip-level assistant for trip-wide changes, and the day-level assistant for stop-specific changes
Frequently Asked Questions
Does the assistant work offline?
Yes. Apple Intelligence runs entirely on your device and does not require an internet connection.
Will the assistant's changes affect shared copies of my trip?
Yes. Changes made by the assistant are saved to your trip and sync via iCloud, so anyone with whom you've shared the trip will receive the updates.
What if the assistant makes an unwanted change?
You can ask the assistant to undo or reverse what it just did: "Actually, put the name back to what it was" works in many cases within the same session. If the session has ended, use the AI assistant in a new session or re-import the trip from a JSON file if you have one.