Field Notes: The trip that lived in three apps

I didn’t set out to build a travel app. I set out to stop opening three different apps every time I took a trip.

That’s the honest origin of Wendways. It started as a fix for my own problem, and I suspect a lot of travelers have the same one. I like things together in one place. For years, my travel life wasn’t.

The itinerary app

For a long time, I used TripIt. And to be fair to it, TripIt was great at the thing it’s known for. I’d forward an itinerary email, and a tidy plan for the trip would appear, flights and hotels and all, without me typing a thing. I still think forwarding your bookings is one of the best ideas in travel software.

But as an everyday traveler using it for my own trips, I felt like the experience hadn’t moved forward much in ten or fifteen years. That original idea was still good. I just wasn’t seeing much innovation that changed how I planned or kept track of my travels.

What I found, too, was that for me it stayed pretty self-contained. Once a trip was underway, I mostly opened it to check what was next. When the trip was over, it went quiet.

The flight log

At the same time, I was logging my flights on openflights.org. Every flight, plus the tail number and the seat I sat in. I’m a bit strange that way. I know.

OpenFlights is a genuinely lovely tool for people like me. Seeing years of flights drawn across a map scratches an itch nothing else quite does.

The gap in the middle

The trouble was that, for me, the two didn’t really talk to each other. Yes, OpenFlights does offer a TripIt plugin that makes importing trips easier. Even so, I was still using two separate tools, with my itinerary and flight log living apart. So keeping my flight history complete became one more chore I had to remember after every trip.

Neither tool was doing anything wrong. They were built for different jobs. I just wanted those jobs to happen in the same place.

The third problem: who paid for what

Then there’s the part of travel nobody puts on a postcard: money with friends.

If you’ve traveled in a group, you know how it goes. One person pays for the house. Someone else covers dinner. Somebody grabs the taxi and says “get me later.” By the end, settling up is a real pain, and it always seems to happen when everyone’s tired and heading home.

My friends and I used Splitwise for this, and it does the job. Plenty of people love it. For me, though, it was frustrating. It was hard to justify paying for a tool I only needed for a handful of trips a year, and the free version limits you to 4 expenses a day. And honestly, it was yet another app for me to manage, sitting off to the side of the trip itself. It also meant asking my travel companions to register for another app if they wanted access to the itinerary, bookings, and shared expenses.

So I put it all together

That’s where Wendways was born. I wanted one place where a trip could live from start to finish: the bookings, the journey, the money, and the record afterward, without me stitching it together by hand across different logins.

Here’s what it does today.

Bookings come in the way I always liked. Forward a booking email to Wendways, or send it a screenshot, and it reads the details and adds them to your trip.

Your old history comes with you. If you’ve been logging flights in OpenFlights or keeping trips in TripIt, you can import that history, so your record doesn’t start from zero.

Everything lands on one map. Flights, trains, ferries, and road trips all count toward a lifetime map and stats, so you see the whole picture of how you’ve traveled, not just the flights.

Expenses live inside the trip. Expense tracking and splitting comes with a paid plan. You log who paid for what right next to the plans it belongs to, and settling up doesn’t need a separate app.

Sample trip. Cover photo by Phil Evenden on Pexels.

I still have a soft spot for the tools that got me here. Each of them did its job well, and they shaped how I think about travel. Wendways is my attempt to put those pieces in one home, for me and, I suspect, for a lot of you.

What’s next?

I’m not stopping here. There’s a lot more planned for Wendways, and I’m excited to get it into people’s hands. I want to build the best travel companion I can: something you can rely on before you leave, while you’re away, and long after you’re home.

That means more than adding features. It means paying attention to the little things that make travel easier, including the ones I haven’t thought of yet. That’s where hearing from other travelers matters.

If that sounds like your travel life too, take a look at wendways.com. And if you’ve got your own version of the three-app shuffle, I’d genuinely love to hear about it.

Chris