Sidetrip Pro unlocks the full power of the app — from creating unlimited trips to generating complete itineraries with on-device AI. 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 | ✓ | ✓ |
| Unlimited trips | — | ✓ |
| AI trip generation | — | ✓ |
| AI assistant (inside trips and days) | — | ✓ |
| Accept shared trips (when at trip limit) | — | ✓ |
| Share trips with others | — | ✓ |
| CarPlay app access | — | ✓ |
Pro Features 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 devices running iOS 26 / macOS 26 with Apple Intelligence support, Sidetrip Pro lets you generate a complete itinerary just by describing your trip. The AI builds out every part, day, stop, accommodation, and transportation segment — all on your device, with no data sent to external servers.
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 AI assistant is available inside any trip or day view. It 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"
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.
How to Purchase
From Settings
- Open Sidetrip on your iPhone, iPad, or Mac
- Go to the Settings tab
- Tap or click Upgrade to Pro
- 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 or tapping Generate with AI — 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 in the Settings tab. A Pro badge confirms your subscription is 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
- Go to 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.
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?
AI features are available to all Pro subscribers, but they 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, and CarPlay access.