Welcome to Sidetrip, the travel planning app that lets you build beautiful, detailed itineraries on your iPhone, iPad, and Mac, then keep them close with the Apple Watch companion. This guide will help you get up and running quickly.
What is Sidetrip?
Sidetrip is a native Apple app for planning and experiencing trips. Whether you're organizing a weekend getaway or a multi-week adventure, Sidetrip lets you map out every day — from morning stops to evening accommodations — and track your progress as you travel. Your trips sync privately across all your Apple devices via iCloud.
Requirements
- iPhone or iPad running iOS/iPadOS 18.0 or later, or
- Mac running macOS 15.0 (Sequoia) or later
- Apple Watch running watchOS 11.0 or later for the Sidetrip Pro companion
- An iCloud account (for syncing trips across your devices)
Apple Intelligence features (AI trip generation and AI assistant) require iOS 26 / macOS 26 or later on a supported device.
Quick Setup Guide
Step 1: Download and Install
Download Sidetrip from the App Store on your iPhone, iPad, or Mac. The app is a universal purchase that works across your Apple devices. Sidetrip Pro also unlocks the Apple Watch companion; use the same iCloud account on your Watch.
Step 2: Create Your First Trip
Tap the + button on the trips list to open Create with AI. You have two ways to create a trip:
- Generate with External AI: Plan your trip with ChatGPT, Claude, Gemini, or any other AI, then tap Get Prompt and paste the prompt into the same conversation. Bring the AI's JSON reply into Sidetrip with Paste from Clipboard or Import Trip File. You can also use these buttons to import any Sidetrip trip file.
- Apple Intelligence: Describe your trip and tap Generate Trip to have Apple Intelligence build a complete itinerary for you (on device on iOS 26 / macOS 26; Apple Private Cloud Compute on iOS 27 / macOS 27 or later)
Step 3: Explore Your Itinerary
Once a trip is created, tap it to open it. Use the sidebar to navigate between the trip overview and individual days, grouped by part. Tap any stop to see full details, directions, website, opening hours, and more.
Step 4: Travel and Track
As you travel, tap the circle next to a stop to mark it as In Progress, Visited, or Skipped. Sidetrip tracks your day's progress and lets you add personal notes to any stop, accommodation, or transportation booking.
Tip: Turn on Settings → Trips → Open Current Trip at Launch and Sidetrip opens the trip you're on, on today's day, every time you launch the app.
Main Features Overview
Trips List
The home screen shows all your trips, separated into My Trips (trips you created) and Shared with Me (trips others have shared with you via iCloud). Use the Sort & Group menu in the toolbar to sort trips by start date or title, turn grouping of shared trips on or off, and show archived trips, which are hidden by default.
Trip Detail View
Opening a trip shows the full itinerary in a sidebar/detail layout. The sidebar lists the trip overview, then each Part (a named segment of the trip) and its days. Select a day to see its timeline of stops and bookings, accommodation, tips, and a map of all locations.
Cover Photos
Give a trip or any of its days a cover photo from your photo library or Files. Covers appear at the top of the trip overview and day view, sync through iCloud, and are shared with everyone who has access to the trip. Adding photos is free. With Sidetrip Pro on iOS 27 / macOS 27 or later, you can also create a cover with Image Playground.
Parts and Days
A trip is divided into Parts — logical segments like "Rome" or "Day Trips from Florence" — each containing one or more days. This structure keeps long trips organized and easy to navigate.
Stops
Each day contains a series of Stops — individual activities or places, each with a time, category (attraction, food, scenic, transport, stay), description, address, map pin, website, opening hours, cost, and more. The day view shows them as a timeline with start and end times and the travel time between stops. You can add personal notes to any stop and track your visit status.
Accommodations and Transportation
Each trip also includes a full list of accommodations (with check-in/check-out dates and map links) and transportation segments (flights, trains, buses, ferries, car rentals) for easy reference while traveling.
AI Trip Generation
On supported devices, Generate with AI creates a full multi-day itinerary from a simple description. 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 for processing. PCC requires internet access and is subject to Apple's daily usage quota. Sidetrip shows failures without silently switching models or processing locations. Generation is available to Free and Pro users within their trip limits; Pro does not increase or remove Apple's quota.
AI Assistant
The Pro-only AI assistant is available inside any trip or day view on supported devices. Ask it to rename stops, update descriptions, adjust times, add or remove activities, and more using natural language. It appears on your own trips and on shared trips you can edit. On iOS 26 / macOS 26 it runs on your device. On iOS 27 / macOS 27 or later you choose: On Device works offline, while Private Cloud uses Apple Private Cloud Compute to plan and edit your whole trip, requiring internet access and using Apple's daily quota.
iCloud Sync and Sharing
Your trips sync automatically across all your Apple devices via iCloud. You can also share any trip with other iCloud users, giving them a live copy that stays in sync.
Apple Watch Companion
With Sidetrip Pro, open the Watch app to browse active trips, days, stops, accommodations, and transportation details. While a trip is in progress, the Up Next card shows your next stop so you can tap Start and Mark Visited as you go. Downloaded trips remain available when you are offline and sync when the connection returns.
Trip creation, JSON import/export, maps, navigation, sharing management, and AI features are available in Sidetrip on iPhone, iPad, or Mac rather than on Apple Watch.
Need help? Browse our knowledge base for more detailed guides.