What is Tripsy?
Tripsy is an iPhone, iPad, Mac and Apple Watch app for organising flights, stays, activities, documents and expenses into a day-by-day itinerary. Version 3.10 (14 September 2026) added Smart Import, which turns photos, screenshots, documents, pasted text, map lists and supported web or social links into places and reservations, and Smart Insights, which pulls details such as baggage, breakfast and cancellation terms from attached documents and emails. Through its MCP server Tripsy also connects to AI assistants such as Claude and ChatGPT, where it is now in the official plugin directory, to create and edit trips by conversation.
Cost: Free + paid plan (Paid from US$7.99 per month). Booking: No booking. Works on: iPhone, Mac or Windows app, Web, App in ChatGPT.
Best for: Apple users whose bookings and ideas are scattered across email, screenshots and map lists and who want one tidy itinerary.
How Tripsy uses AI
Smart Import uses Tripsy's own processing server and a range of models to extract places and bookings from messy inputs; Smart Insights runs on-device with Apple Intelligence; the MCP connector lets an outside assistant create trips, add activities and update itineraries in your account.
Booking: No booking.
Keep in mind
- No native Android app (waitlist only); the web version can view itineraries but not create or edit them
- Smart Import and Smart Insights are Pro features; Smart Insights needs a device that supports Apple Intelligence
- Tripsy organises plans but does not book travel or take payments
Is Tripsy free? Cost and plans
Free + paid plan. Free tier with unlimited trips; Tripsy Pro adds Smart Import, Smart Insights, flight alerts and more. The US App Store also lists several older Pro and Premium price points.
| Plan | Price | Region | Checked |
|---|---|---|---|
| Tripsy Pro (one year) | US$59 per year | Not stated (USD shown on tripsy.app) | Source, |
| Tripsy Pro (lifetime) | US$299 one-off | Not stated (USD shown on tripsy.app) | Source, |
| Tripsy Pro: Monthly (App Store) | US$7.99 per month | US | Source, |
Prices are shown in the currency and region the provider published. We do not convert them.
Tripsy alternatives
Tools for a similar task. Sharing a task does not make them interchangeable, so compare what each one does.
Sources
Sources checked . This listing summarises what the provider and other cited sources say; it is not a hands-on test.
- Tripsy: Travel Planner (App Store, US)apps.apple.com, checked . Supports: Feature list including Smart Import (online processing, Pro), Smart Insights (on-device, Apple Intelligence) and 'Plan with your AI assistant'; iPhone, iPad, Mac and Apple Watch; in-app purchase prices; updated 9 October 2026
- Tripsy Pro – What's Included, Price & Buy Optionstripsy.app, checked . Supports: Free tier; Pro US$59 for one year; Lifetime US$299 one-time; Pro feature list
- Tripsy 3.10: Set Your Travel Inspiration Free (Tripsy Blog, 14 September 2026)tripsy.blog, checked . Supports: Smart Import uses Tripsy's own processing server and a range of models; Smart Insights runs locally and needs Apple Intelligence; both are Pro features; blog index shows 'We're an Official ChatGPT Plugin!' (12 October 2026)
- Tripsy MCP — Connect Your AI to Your Travel Planstripsy.app, checked . Supports: Hosted MCP server; Claude connector directory; build and update trips by conversation; adding items does not book travel or make a payment; document features depend on Pro
- Tripsy + ChatGPTtripsy.app, checked . Supports: Install the Tripsy plugin in ChatGPT to create and reorganise itineraries in conversation
- Tripsy for Androidtripsy.app, checked . Supports: No native Android app yet; itineraries viewable in a browser; Android waitlist
- Tripsy for Webtripsy.app, checked . Supports: Web view of itineraries at my.tripsy.app; create and edit in the app
What we could not confirm
- Whether the MCP connector or ChatGPT plugin requires Tripsy Pro
- Which ChatGPT plans can use the Tripsy plugin
- Which models Smart Import uses