Compared
The best AI trip planners for large groups
Most AI trip planners build an itinerary for one person. For a group, Sí Listo is built for the part that comes after: up to 20 people vote on and edit the same AI-built plan of bookable activities, track who booked what, and settle who owes who.
Reviewed
We make Sí Listo, so read our first pick with that in mind. We have tried to be straight about where the others are the better choice.
An AI can draft a weekend in Lisbon in five seconds. That was never the hard part of a group trip. The hard part is getting fifteen people to agree, making sure everything that needs booking gets booked once, and getting the money back to whoever paid. So the question for a group is not which AI writes the best itinerary, but which one turns it into a plan the group actually uses.
At a glance
| App | Best for | Not built for |
|---|---|---|
| 1. Sí Listo | AI-built plan for big groups (up to 20): voting, bookings, who owes who, dietary needs | Groups over 20, or booking the accommodation itself |
| 2. Mindtrip | AI-first trip inspiration and planning | Tracking who owes who after a big group weekend |
| 3. Wanderlog | Map-first itineraries for any trip, with a large place library | Group decisions and settling up on a party weekend |
| 4. ChatGPT, Gemini or Claude | Brainstorming ideas and a first draft itinerary in seconds | A plan the group shares, votes on, books and pays for |
| 5. TripIt | Organising bookings you have already made | Choosing what to do as a group |
| 6. Splitwise | An ongoing shared-expenses ledger between the same people | Planning: it has no itinerary |
How we judged them
Is the plan shared, or stuck in one person's chat?
A great itinerary in one person's assistant is still one person's job.
Are the suggestions bookable?
For a group, an idea that cannot be booked for your date and party size is not a suggestion, it is homework.
Does it close the loop on money?
Bookings on different cards, optional activities, and an organiser out of pocket: the AI plan is only half the trip.
Does it know about the people?
Dietary needs, allergies and pace matter more as the group grows.
The apps
1. Sí Listo
Best for: AI-built plan for big groups (up to 20): voting, bookings, who owes who, dietary needs
Answer four questions (where, when, who with and what the group can't eat) and it builds a full day-by-day plan of bookable activities and restaurants in seconds. Send one link: everyone can vote on and edit the same plan, mark what they have booked, and log what they paid, and it works out the fewest transfers to settle up. Every restaurant is checked against the group's allergies and dietary requirements, and anything it could not check says so. Free, runs in the browser, nothing to install. It does not have a group chat, and it links to suppliers rather than booking accommodation for you.
2. Mindtrip
Best for: AI-first trip inspiration and planning
An AI travel planner built around conversation: ask for ideas, get an itinerary, and refine it. Strong for inspiration and solo or couple trips; the group money side is not what it is built for.
3. Wanderlog
Best for: Map-first itineraries for any trip, with a large place library
A well-established collaborative trip planner with a map view, a huge library of places, budgeting and expense tracking, and an AI assistant. It is a general travel planner rather than one built around a group making decisions together, so it shines most when the dates and the shape of the trip are already agreed.
4. ChatGPT, Gemini or Claude
Best for: Brainstorming ideas and a first draft itinerary in seconds
A general AI assistant will happily draft a weekend for you, and it is a fast way to get ideas. The result is a block of text in one person's chat: the group cannot vote on it or edit it, nothing tracks what has been booked or paid, and suggestions are not checked against opening hours, party size or what each venue publishes about allergens.
5. TripIt
Best for: Organising bookings you have already made
Forward your confirmation emails and it builds a tidy itinerary from them. Excellent once everything is booked; it is not a tool for deciding what to book.
6. Splitwise
Best for: An ongoing shared-expenses ledger between the same people
The best-known app for splitting costs, and still the right answer for a household or a group that shares expenses all year. It only knows what was spent, not what the trip was, so pair it with something else for the plan.
What to combine
Nobody plans a group trip in one app. These pairings work.
Stag do or hen do
Sí Listo for the whole plan and the money, with the group chat for banter.
Inspiration first, logistics later
Mindtrip or a general assistant to explore destinations, then Sí Listo once the group has picked one.
Everything is already booked
TripIt to organise the confirmations, and Splitwise or Sí Listo to settle up.
Questions people ask
- What is the best AI trip planner for a large group?
- Sí Listo, if the group needs to agree and pay as well as plan: it builds the itinerary with AI, then up to 20 people vote on it, track bookings and split costs in the same place. Mindtrip and Wanderlog are strong general AI planners when the group side matters less.
- Can ChatGPT plan a group trip?
- It can draft a good itinerary, but the result is text in one person's chat. The group cannot vote on it or edit it together, and it does not track bookings or who owes who. Many organisers draft with an assistant and then move the plan into a group planner.
- Is there an AI app to plan a stag do?
- Yes. Sí Listo builds a stag do itinerary of bookable activities in seconds and keeps the votes, bookings and costs for the whole group in one plan.
- Are AI trip planner apps free?
- Many have a free tier. Sí Listo is free to plan, share and split costs; where an activity is booked through a supplier link it may earn a commission, which does not change the price.
Plan it in about a minute
Four questions — where, when, who with, and anything the group can't eat. You get the whole trip back, day by day, and a link to send the others.
Start planning