Tripsy
Co-founder & Developer
2018 — Present
My cofounder and I have been building Tripsy since 2018, helping people plan and organize their travels. It brings itineraries, reservations, and travel details together, making it easier to plan a trip and share it with others.
Visit Tripsy or download the app.
Building Tripsy
Tripsy started with a long trip to Italy I was planning in 2018. I had several hotels booked and lots of places I wanted to visit, and I needed a better way to keep everything organized and easy to access, even offline.
My cofounder and I built Tripsy around that need. Since then, it has grown into a complete tool for travel planning and organization. Today, that also includes MCP integration, making it possible to work with AI agents on travel plans.
It’s still the app I use to plan and organize my own trips. Here are a few milestones along the way:
- 2018: My cofounder and I started building Tripsy.
- 2019: Tripsy 2.0 brought the trip-planning experience reviewed in depth by MacStories, including collaboration, travel documents, and integration with Apple platforms.
- 2024: Tripsy 3.0 appeared in The Verge’s Installer. Later that year, Apple named Tripsy an iPhone App of the Year finalist.
- 2026: We introduced smarter imports and on-device AI insights, covered by 9to5Mac.
Recognition from Apple
2024 iPhone App of the Year finalist
Apple named Tripsy an iPhone App of the Year finalist at the 2024 App Store Awards, recognizing its role in helping travelers stay organized.
Mentioned in Apple’s Siri AI announcement
In September 2026, Apple included Tripsy in its introduction of Siri AI, describing adding a restaurant recommendation to Tripsy as an upcoming app action.
Read Apple’s Siri AI announcement.
Selected press coverage
- MacStories — Tripsy Review: The Ultimate Trip Planner for iPhone and iPad — Ryan Christoffel, October 2019. An in-depth review of Tripsy 2.0, covering trip planning, collaboration, document storage, and integration with Apple platforms.
- 9to5Mac — Smarter imports and on-device AI insights — September 2026.
- BGR — Simplify Your Next Big Trip With The Latest Update To Tripsy For iPhone — August 2025.
- Canaltech — Como usar o Tripsy para planejar viagem — January 2025. A guide in Portuguese.
- TechRadar — Apple’s 2024 app finalists — November 2024. Includes a section on Tripsy.
- The Verge — Tripsy 3.0 featured in Installer — September 2024. A recommendation in the newsletter’s “The Drop” roundup.
More reading & watching
MacStories
- Web-based itineraries and expanded travel email forwarding
- Weather forecasts, time zones, and customization
- I Let Tripsy and Claude Plan My Weekend Away — Members-only.
9to5Mac
- Tripsy coverage from February 2025
- Tripsy’s customizable trip overview — October 2024.
- Organizing everything you need to plan a great trip — June 2020.
- An all-in-one iOS travel app — January 2019.
Elsewhere
- TWiT — iOS Today, episode 695
- MacRumors — 2024 App Store Awards finalists
- iHelp BR — Tripsy travel planner — Portuguese.
- TugaTech — AI integration for travel planning — Portuguese.
- TugaTech — Tripsy 3.8 and calendar integration — Portuguese.
- Kölner Stadt-Anzeiger — Six tablet apps for your vacation — German.
- Soy de Mac — An introduction to Tripsy — Spanish.