Welcome to Sidetrip, the travel planning app that lets you build beautiful, detailed itineraries on your iPhone, iPad, and Mac. 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
- 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 all your Apple devices.
Step 2: Create Your First Trip
Tap the + button on the trips list to add a new trip. You have three ways to create a trip:
- Generate with AI: Describe your trip and let Sidetrip's on-device AI build a complete itinerary for you (requires a supported device with Apple Intelligence)
- Import from JSON: Paste or load a Sidetrip-format JSON file to populate a trip in seconds
- Use the AI Prompt: Copy a structured prompt and use it with any AI assistant to generate a compatible JSON file, then import it
Step 3: Explore Your Itinerary
Once a trip is created, tap it to open the trip detail view. Use the sidebar to navigate between parts and individual days. Tap any stop to see full details, a map, website, opening hours, and more.
Step 4: Travel and Track
As you travel, tap stops to mark them as In Progress, Visited, or Skipped. Sidetrip tracks your day's progress and lets you add personal notes to any stop.
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). You can sort trips by start date or alphabetically by title. Archived trips are hidden by default but can be shown with the toggle in the toolbar.
Trip Detail View
Opening a trip shows the full itinerary in a sidebar/detail layout. The sidebar lists each Part (a named segment of the trip) and its days. Select a day to see its stops, accommodation, tips, and a map of all locations.
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, transport, scenic), description, address, map pin, website, opening hours, cost, and more. 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, the Generate with AI option uses on-device Apple Intelligence to create a full multi-day itinerary from a simple description. Everything runs on your device — no data is sent to external servers.
AI Assistant
The AI assistant is available inside any trip or day view. Ask it to rename stops, update descriptions, adjust times, add or remove activities, and more — all using natural language.
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.
Need help? Browse our knowledge base for more detailed guides.