Every great trip starts as a group chat. Seventeen notifications in, a Pinterest board nobody's updated since July, a friend who still hasn't Venmo'd for last year's Airbnb — and someone, inevitably, asking "wait, who booked the car?"
The trip always happens. But the getting-there part shouldn't be harder than the trip itself.
Why we built this.
We've taken the trips. We've been the friend running the spreadsheet. We've also been the friend who silently resented the spreadsheet. Planning a group trip inside a group chat is like trying to cook Thanksgiving dinner over text message — technically possible, spiritually ruinous.
The group chat is great for bad jokes at 1 AM. It is not an itinerary. It is not an expense tracker. It is not a place where decisions live. Every time we tried to force it into those jobs, something broke — usually a friendship, always a booking window.
Seven unread threads. Four half-booked flights. The trip always happens — the getting-there part shouldn't feel harder than the trip itself.
RoundTrips is what we wanted the group chat to be. A shared itinerary that updates for everyone the moment someone changes it. Expenses that balance themselves as you go. Votes that settle the tapas-vs-tacos debate in thirty seconds. A trip roster that actually respects who's in, who's out, and who's only in for the weekend.
What's inside.
Five things that make a trip work.
- 01Shared itineraries that update in real time. Drag a day, drop a pin, see the whole trip on one map. Change a dinner spot and the crew gets the memo.
- 02Expenses, effortlessly. Who paid. Who owes. Settled in one tap — no Venmo-math at the airport.
- 03Live updates. Flight delayed? The group knows. Dinner moved? The group knows. Nobody gets stranded.
- 04Voting. Beach day or hike? Tapas or tacos? Polls settle it — without the three-hour debate.
- 05RSVP, per leg. In for the whole trip, out for the hike, back for dinner. RoundTrips handles the math so nobody has to be the "hey, about the deposit…" person.
The bigger idea.
We're not trying to replace the trip. The trip is the point. We're trying to replace the mess around it — the coordination, the spreadsheet, the "I'll Venmo you later" economy of unsaid debts. So the group chat can go back to being what it does best: a place for bad jokes at 1 AM, unsolicited flight screenshots, and photos nobody asked for of somebody else's dinner.
Good tools should feel like part of the experience, not a layer on top of it. RoundTrips is built to disappear into the trip, not to be another thing to manage.
Who built this.
RoundTrips is part of The HowTo Network — a family of editorial-first platforms for the things people actually do together. We believe travel is better when it's shared, and tools are better when they respect the way people already live.
We're a small team, building in the open, shipping fast. The beta is free. It will stay free for crews using it now.
Partnerships, press, or hi.
Working on something we should know about? Writing a story? Want to bring RoundTrips to your community? We read every email.
✉ partnership@thehowtonetwork.com