Every few months a new AI travel app promises to plan your entire trip in thirty seconds flat. Some of them are genuinely good at it. But there’s a question none of them quite answer: once the itinerary exists, where does it actually live — and what happens to it on day three, when your flight is delayed and you’re standing in a foreign airport trying to remember which hotel confirmation email had the address?
Locals Insider asked Thiago Sanchez, co-founder of Tripsy, to make the case for the other half of the trip-planning problem — the part that starts after the AI chat window closes.
Tripsy has spent eight years building the organizational layer underneath the trip: the app that turns forwarded booking emails into a real itinerary, syncs your calendar across time zones, and lets a family coordinate a group trip without anyone losing control of it.
In 2024, Tripsy was named a finalist for Apple’s App of the Year, one of 45 apps recognized globally. Here is Sanchez’s own account of why he thinks organizing a trip is a fundamentally different — and, in his view, harder — problem than generating one, in his own words.
The Post-it Wall
Tripsy started in a work meeting in 2018. My co-founder Rafael and I worked at the same company, and one day during a meeting he noticed a wall of Post-its behind my desk and asked what they were. I told him I was planning a big trip across Europe and had hit a wall of frustration — no app actually organized it.
I had Post-its, browser tabs, a Google Doc, scattered confirmation emails. A mess. He looked at me and said, “I’m building an app for exactly that.” That was it. We started building Tripsy from that conversation.
What we were both feeling was the same gap. Trip planning tools back then were either pure inspiration — beautiful photos, bucket lists — or pure booking engines built around price.
Nobody had built the layer in between: the place where your trip actually lives as something organized and usable while you’re standing inside it. Not a mood board. Not a search engine. A plan. That felt obvious to build. The Post-its were apparently the proof.
What Changed, and What’s Just Hype
The technology around us changed dramatically over the last two years. The hard problem didn’t.
Here’s what changed: the cost of generating a plausible-sounding itinerary dropped to nearly zero. Any competent developer can wire up an LLM this weekend and produce “Day 1: arrive in Lisbon, visit Belém Tower, dinner in Mouraria.” That’s why you’re suddenly seeing dozens of these apps.
We understand this shift deeply — we built native integrations with Claude and a Tripsy MCP that lets you connect ChatGPT, Claude, or any custom LLM connector and plan a trip through natural conversation. We did that because LLMs are genuinely powerful for part of this problem. The keyword there is part.
Here’s what Tripsy actually solves: the moment you’re on the trip. I want to open my itinerary and see the weather for each day, not open a separate app to check it. I want to glance at a layover and instantly know how many hours I have at that airport, without doing the math myself.
I want to see at a glance that I have a totally free day with nothing planned, so I can decide what to do with it. I want a map showing everything I’ve saved, plotted around my hotel.
I want to share the trip with my wife and actually hand her real control of it, not send her a PDF she can’t touch. I want to share with extended family and choose exactly what they see — the itinerary, sure, but maybe not the expenses or the documents.
None of that comes out of a chat window.
The hype is that AI itinerary generation is the product. It’s not. It’s a good feature — we built one ourselves. But a pre-generated itinerary is a starting point, not a destination.
The actual product is the organized, living plan you stay in control of: one you can adjust, share selectively, check on a map, and hand off to someone else without losing the thread. The companies that stop at generation are going to struggle to explain what they do on day two of your trip.
Why Not Just Ask ChatGPT?
AI tools are genuinely useful for planning, and I mean that honestly — if you want a rough draft itinerary for a week in Tokyo, ChatGPT will do that well. We don’t argue with that. We built our own integration specifically because we agree with it.
But here’s the real question: once you’ve planned the trip, where does all that information actually live? Think about a twenty-day trip through China — flights, internal trains, hotels across six cities, restaurants, documents, expenses.
That’s an enormous amount of information to keep in a chat thread. I say this after eight years building a travel planner and more than a decade of heavy travel myself: a trip can go seriously wrong without a proper plan. And even when you think you have no plan, you actually do.
You have flights booked, a hotel for the first night, a few places you already want to see. That’s a plan. It just needs somewhere to live.
That’s where our AI integration gets genuinely useful. Tripsy connects to Claude, ChatGPT, or any LLM through our MCP, so you’re never locked into one AI. And you’re not just generating ideas and copy-pasting them into a notes app somewhere.
Ask for recommendations in whichever AI you already prefer, and Tripsy organizes the results directly into your trip — structured, dated, and ready, the moment you open the app.
Who Actually Comes Back a Third Time
The traveler who uses Tripsy for a third trip in a row isn’t the impulse traveler. It’s someone who feels something close to anxiety when a trip becomes a mess of scattered browser tabs and forwarded emails.
They usually take two to five trips a year — travel matters to them, but it isn’t their job. They care about the experience, not just the destination checkbox. And there’s almost always someone else in the picture: a partner, a group of friends, someone they’re actively coordinating with.
What were they using before Tripsy? Usually some mix of a shared Google Doc, TripIt, and a long email thread. Or just tolerated chaos until they found something better.
The person who downloads an app once and disappears is usually chasing pure inspiration — they want to dream about travel, not organize it. We’re not primarily an inspiration tool. We’re a planning and organizing tool. Those are genuinely different products, and a lot of travel apps get that distinction wrong.
We Don’t Try to Guess What Kind of Traveler You Are
People ask how Tripsy figures out what kind of traveler someone is, so we can personalize suggestions. Honestly — we don’t. That’s deliberate.
There are already excellent systems whose entire job is recommending places or generating ideas. Our job is different.
We’re building the place where everything from your trip comes together and lives well: flights, hotels, activities, documents, expenses, all organized and easy to navigate. The value isn’t in what Tripsy suggests to you. It’s in what you bring to it, and how well we keep it.
Every trip is different because every traveler organizes information differently. Some people care most about restaurants, others about trains, others about museum reservations. Instead of guessing what matters to you, we let you build the trip your way and make sure managing it stays effortless.
You don’t even need to create an account to start using Tripsy — we never wanted to be one more complicated thing standing between you and a trip you’re already stressed about planning. Travel is enough work on its own. The app should feel like relief.
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