Sidetrip Pro unlocks the full power of the app — from creating unlimited trips to planning and editing itineraries with the AI assistant. This guide explains what's included and how to get Pro.
Free vs Pro Comparison
| Feature | Free | Pro |
|---|---|---|
| Create and view trips | ✓ (1 trip) | ✓ (unlimited) |
| Full itinerary detail (parts, days, stops) | ✓ | ✓ |
| Stop visit tracking (visited, in progress, skipped) | ✓ | ✓ |
| Personal notes on stops | ✓ | ✓ |
| Maps, addresses, websites, opening hours | ✓ | ✓ |
| Accommodations and transportation details | ✓ | ✓ |
| iCloud sync across devices | ✓ | ✓ |
| Import trips from JSON | ✓ | ✓ |
| Archive trips | ✓ | ✓ |
| Trip and day cover photos | ✓ | ✓ |
| Open the current trip at launch | ✓ | ✓ |
| Unlimited trips | — | ✓ |
| AI trip generation | ✓ (within trip limit) | ✓ |
| AI assistant (inside trips and days) | — | ✓ |
| Accept shared trips (when at trip limit) | — | ✓ |
| Share trips with others | — | ✓ |
| CarPlay app access | — | ✓ |
| Apple Watch companion app | — | ✓ |
| AI-generated covers (iOS 27 / macOS 27 or later) | — | ✓ |
| Alternate app icons (iPhone and iPad) | — | ✓ |
Feature Access Explained
Unlimited Trips
The free tier allows one trip (counting both your own trips and trips shared with you). With Pro, you can create and store as many trips as you like — past adventures, upcoming plans, and everything in between.
AI Trip Generation
On supported devices with Apple Intelligence, both Free and Pro users can generate complete itineraries within their existing trip limits. Generation runs locally 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 for processing. PCC requires internet access and is subject to Apple's daily usage quota. Pro does not increase or remove that quota, and Sidetrip shows failures without silently switching models or processing locations.
Simply tap Generate with AI when creating a new trip, describe where you're going and for how long, and Sidetrip does the rest.
AI Assistant
The Pro-only AI assistant is available inside any trip or day view on supported devices. On iOS 26 / macOS 26 it runs on your device. On iOS 27 / macOS 27 or later you choose On Device, which works offline, or Private Cloud, which plans and edits your whole trip using Apple Private Cloud Compute. Private Cloud requires internet access and uses Apple's daily quota, which Pro does not increase. The assistant can understand and execute natural-language requests like:
- "Rename Day 3 to 'Coastal Drive'"
- "Update the tagline for this trip"
- "Add a dinner stop at 7pm on the last day"
- "Remove the museum visit on Day 2"
- "Change the description for the Eiffel Tower stop"
- "Fill day 4 with things to do near the hotel" (Private Cloud)
The assistant remembers the context of your conversation so you can make multiple edits in a single session. When the session is full, tap New Session to start fresh.
Sharing Trips
With Pro, you can share any trip with other iCloud users. They receive a live copy that updates whenever you make changes. Sharing is a great way to coordinate travel plans with a partner, family, or group of friends.
CarPlay
Sidetrip Pro unlocks the CarPlay app, which lets you browse trips, open days, view stops, and start navigation from your vehicle's CarPlay display.
Apple Watch Companion
Sidetrip Pro unlocks the Apple Watch companion on watchOS 11 or later. Browse active private and shared trips, review days, stops, accommodations, and transportation, and track your progress from your wrist. While a trip is in progress, the Up Next card shows your next stop with Start and Mark Visited buttons.
You can update a stop's visit status when you have permission to edit the trip. The Watch app does not create or import trips, edit itinerary content, show maps, start navigation, manage sharing, or provide AI features. Use the main app on iPhone, iPad, or Mac for those actions.
AI-Generated Covers
Anyone can add a photo or image file as a trip or day cover. On iOS 27 / macOS 27 or later, Sidetrip Pro also lets you tap Generate with AI in the cover editor to create a cover with Image Playground, using ideas from the trip or day. Image Playground must be available on your device.
Alternate App Icons
On iPhone and iPad, Pro unlocks alternate app icons in Settings → App Icon. You can always switch back to the default icon.
How to Purchase
From Settings
- Open Sidetrip on your iPhone, iPad, or Mac
- Open Settings — the gear button on the trips list on iPhone and iPad, or Sidetrip → Settings in the menu bar on Mac
- Tap or click the Sidetrip Pro card
- Confirm your one-time purchase with Face ID, Touch ID, or your Apple ID password
From a Pro Feature
When you try to use a Pro feature — like creating a second trip, tapping Share Trip, or opening the Assistant — Sidetrip will offer you the option to upgrade. Tap the upgrade button to proceed directly to the purchase screen.
Pricing
Sidetrip Pro is available as a one-time purchase through the App Store. Check the app for current pricing.
Your purchase includes:
- Lifetime access to all Pro features
- All future Pro feature updates
- Use on all your Apple devices signed into the same Apple ID
Managing Your Purchase
View Pro Status
Your Pro status is displayed at the top of Settings. When Pro is unlocked, it shows Sidetrip Pro — Active.
Restore Purchases
If you've already purchased Pro and need to restore it (after reinstalling the app or on a new device):
- Open Sidetrip
- Open Settings
- Tap Restore Purchases
- Wait for the restoration to complete
Ensure you're signed in with the same Apple ID you used for the original purchase.
Frequently Asked Questions
Does Pro work on all my devices?
Yes. Your purchase is tied to your Apple ID. Any device signed in with the same Apple ID will have access to Pro features after a purchase or restore, including the Apple Watch companion after Pro access syncs through iCloud.
Can I get a refund?
Refunds are handled by Apple through the App Store. Visit reportaproblem.apple.com to request a refund.
Are AI features included for all Pro users?
The assistant requires Pro; generation is available to Free and Pro users within their trip limits. Both require a device and OS version that supports Apple Intelligence (iOS 26 / macOS 26 or later). On older devices, Pro still unlocks unlimited trips, sharing, CarPlay, and the Apple Watch companion. AI-generated covers require iOS 27 / macOS 27 or later and Image Playground. PCC generation on OS 27+ also requires internet access and is subject to Apple's daily quota, which Pro does not increase or remove.