Anywayr wrote this. Group trips are what we build for, so we have also listed the other ways to do it, including ones that do not involve us.
The short answer
An AI assistant is a good way to settle the hard first questions of a group trip: where, when and roughly how much. Where it falls short is everything after. The plan lives in one person's chat, nobody else can vote on it, the prices are estimates, and someone ends up paying for the house and chasing everyone for their share.
Adding the Anywayr connector to ChatGPT or Claude moves the plan out of the chat and onto a trip page the whole group can open. Friends vote on the stays and plans there, Anywayr tracks who owes whom, and hotels and flights can be searched, quoted and booked from the same trip.
The usual way, and where it breaks
Most groups do some version of this:
- One person asks ChatGPT or Claude for ideas and gets a good itinerary.
- They screenshot it into the group chat.
- Five people reply with opinions on different messages.
- Someone books a place, pays for all of it, and keeps a note of who owes what.
The assistant did its part well. The trouble is the handoff. A screenshot cannot be voted on, the prices in it go stale, and the money sits with one person.
A better way with an assistant and Anywayr
1. Agree the basics in the chat
Ask the assistant the open questions first. "Six of us, a long weekend in June, two flying from Chicago and four from Boston, around $1,200 each. Where should we go?" You do not need any connector for this.
2. Save the trip
Once you pick a place:
Plan a long weekend in Porto for six friends, June 11 to 14, 2027.
The assistant asks Anywayr to save the trip and gives you its link straight away. A day-by-day plan keeps building on Anywayr after that. The trip starts private to your account.
3. Share the trip page
Open the link and invite your friends to the trip on Anywayr. Everyone works from one trip page and sees the same version of the plan.
4. Vote
Friends vote on stays and plans on the trip page. When three people prefer one place and two prefer another, the votes are on the page, and nobody has to scroll back through the chat to count.
5. Search, quote and book
Back in the assistant:
Find hotels in Porto for June 11 to 14 for two adults.
Anywayr searches one room at a time, so for six people you might search for three rooms. When the group agrees, ask for a quote. It shows the exact total and the cancellation terms, and it expires. The assistant then hands you a link to Anywayr's checkout page. In Claude, VS Code and Codex you can also allow booking with your saved card in the chat, for fully refundable bookings within a limit you set. It is off by default. ChatGPT always uses the checkout link.
Flights work the same way. Anywayr searches by exact route, date, passengers and cabin, up to 9 passengers, so the Chicago pair and the Boston four can each get their own search.
6. Split the costs
Anywayr tracks shared costs on the trip and shows who owes whom, with Venmo and Cash App links to settle up. The person who booked the rooms does not need a spreadsheet.
Checked on 5 Nov 2026. Sources:
- Anywayr, What is Anywayr? and FAQ (trip page, voting, cost splitting).
- Anywayr, MCP server reference, Add Anywayr to Claude and Add Anywayr to ChatGPT; Claude directory, Anywayr.
- Travolp, Use Travolp from Claude and ChatGPT.
- Wanderlog, wanderlog.com.
Other ways to plan a group trip with AI
| Option | Shared plan | Voting | Splitting costs | Books hotels and flights | Works in ChatGPT and Claude |
|---|---|---|---|---|---|
| Assistant on its own, plus a group chat | A screenshot or pasted text | No | No | No | Yes |
| Anywayr connector | A trip page the group opens | Yes, on stays and plans | Yes, with Venmo and Cash App links | Yes, through checkout, or saved card in Claude, VS Code and Codex if you allow it | Yes: Claude directory; ChatGPT developer mode |
| Travolp connector | A trip with a group chat the assistant can read and send to | Not described | Yes, logs shared expenses and shows who owes whom | Not described; its page covers itineraries, places and packing lists | Yes, Claude and ChatGPT |
| Wanderlog | A shared itinerary the group edits live | Not described | Yes, budget and cost splitting between tripmates | Imports reservations and finds lodging | Not described |
"Not described" means the company's own page does not say it; it does not mean the feature is missing.
Where the alternatives are better
- Travolp lets the assistant read and post in your trip's group chat and build a packing list. If your group has already booked and just needs an itinerary and an expense log run from Claude or ChatGPT, it covers that, and connecting it costs nothing.
- Wanderlog is built around editing one itinerary together, with live syncing. If your group likes to plan every stop by hand and has booked elsewhere, it is a strong fit. We compare it in more detail in Anywayr vs Wanderlog.
- The assistant on its own is enough for a trip where one person books everything and nobody minds settling up later.
Where Anywayr is better
- Planning, voting, booking and paying back in one place. The other options cover some of these. Anywayr connects them to real hotel and airline prices.
- The assistant does the legwork. You stay in ChatGPT or Claude for the questions and the searches, and the group sees the result on the trip page.
- Clear limits on what the AI can do. You choose on the Anywayr connect screen what the assistant may do, and you can approve less than it asks for.
The honest limits
- Prices are in US dollars.
- Hotel searches and bookings cover one room each, up to 8 adults per room.
- Everyone who votes needs to join the trip on Anywayr.
- No rental cars through the connector.
- In ChatGPT, Anywayr needs developer mode for now; its directory listing is in review.
Get started
Add Anywayr to Claude from the Connectors directory, or to ChatGPT through developer mode. For a walk through of one conversation, read planning a trip in Claude with Anywayr. For other travel connectors, see travel connectors for ChatGPT and Claude.
