The Sidetrip AI assistant lets you plan and 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
- For the Private Cloud assistant: iOS 27 / macOS 27 or later and an internet connection
- Permission to edit the trip. The assistant is available on your own trips and on shared trips you can edit, but not on view-only trips
On Device and Private Cloud
On iOS 27 / macOS 27 or later, a switch at the top of the assistant lets you choose where it runs. Sidetrip remembers your choice and starts with Private Cloud. On iOS 26 / macOS 26, the assistant always runs on your device.
| On Device | Private Cloud | |
|---|---|---|
| Where it runs | On your device, using Apple Intelligence | On Apple Private Cloud Compute (PCC) |
| What it can edit | The trip's details from the trip overview, or a single day from a day view | Your whole trip from anywhere — it can also plan days and suggest places |
| Internet | Not required | Required |
| Daily limit | None | Uses Apple's daily PCC limit, which trip generation also uses |
Each mode keeps its own conversation while the assistant is open, so you can switch back and forth without losing either. Sidetrip never switches modes on its own: if Private Cloud is offline, unavailable, or out of quota, the assistant tells you and offers a Switch to On Device button.
Opening the Assistant
The Assistant button (the Apple Intelligence icon) appears in the toolbar of the trip overview and individual day views. Tap it to open the chat panel.
- From the trip overview: On Device edits the trip's details (name, tagline, dates, day titles and summaries, transportation, accommodations, and the visit status of every stop). Private Cloud can edit everything.
- From a day view: On Device edits that day's stops, title, summary, and tips, and can remove the day. Private Cloud focuses on that day but can still edit the rest of the trip.
What the Private Cloud Assistant Can Do
| Action | Example Request |
|---|---|
| Plan a day | "Fill day 4 with things to do near the hotel" |
| Get suggestions | "Suggest a dinner place near the hotel" (it asks before adding) |
| Move stops between days | "Move the Louvre to Thursday morning" |
| Edit any stop | "Change the cathedral's opening hours to 9:00–17:00" |
| Add or remove days | "Add a rest day after the Sintra day" |
| Change stays and travel | "We now check out of the Lisbon hotel a day later" |
| Add bookings | "Add our train from Porto to Lisbon on the 14th at 10:05" |
| Track progress | "Mark everything today as visited" |
| Ask about the trip | "When do we check out in Kyoto?" |
What the On Device Assistant Can Do
From the Trip Overview
| 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" |
| Change the trip dates | "Move the trip to start on June 12" |
| Edit transportation or accommodations | "Change the flight number to UA123" |
| Mark every stop in the trip | "Reset all stops to not visited" |
From a Day View
| Action | Example Request |
|---|---|
| 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" |
| Edit the day's title, summary, or tips | "Add a tip to book the tower tickets in advance" |
| Update a stop's visit status | "Mark the cathedral as skipped" |
| Remove the day | "Delete this day" (it asks you to confirm) |
Using the Assistant
Making a Request
- Tap Assistant in the toolbar to open the chat panel
- On iOS 27 / macOS 27 or later, choose On Device or Private Cloud
- 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, and each change is listed in the chat. If you remove the day you opened the assistant from, the assistant closes and Sidetrip returns to the trip. The updated trip syncs via iCloud to all your devices. You can see the changes reflected in the trip right away.
Session Limits
Each assistant session has a context window limit. The Private Cloud assistant can hold much longer conversations than the On Device assistant. 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 current mode's conversation and starts a fresh session. All changes you made in the previous session are preserved in your trip — only the conversation context resets.
Apple's Daily Limit
The Private Cloud assistant uses Apple's daily Private Cloud Compute limit, which trip generation also uses. The assistant warns you when you are approaching the limit. When it is reached, it shows when usage resets and any options Apple offers, and you can keep going with On Device. Sidetrip Pro does not increase this limit.
Tips for Best Results
- Be specific about which stop or day: "Rename the Louvre stop" works better than "rename the museum"
- Ask for suggestions first if you're unsure: "Suggest three lunch spots near the Alhambra" lets you choose before anything is added
- 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
- On Device works one scope at a time: Use it from the trip overview for trip-wide details and from a day view for that day's stops. Use Private Cloud for changes that span several days
Frequently Asked Questions
Does the assistant work offline?
The On Device assistant does. It runs entirely on your device and does not require an internet connection for AI processing. The Private Cloud assistant requires an internet connection. Syncing changes via iCloud always requires a connection.
What does the Private Cloud assistant send to Apple?
Your messages and the trip details the assistant needs — such as days, stops, notes, transportation, and accommodations, including confirmation numbers — are sent to Apple's Private Cloud Compute servers for processing. See Privacy & Security for details.
Can the assistant change accommodations or transportation?
Yes. Both assistants can edit transportation and accommodation details from the trip overview. The Private Cloud assistant can also add or remove them and change check-in and check-out dates.
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, describe the change you want in a new session, or restore an exported copy with ⋯ → Update Trip in the trip overview. Exporting the trip before a big round of changes gives you a backup to return to.