PassTheBrief

Plan a trip with AI — and keep the whole plan in one place

AI assistants are good at trip planning: finding flights, suggesting where to stay, drafting a day-by-day plan. The hard part is that a trip takes many conversations, often with different assistants, and the plan ends up in pieces. Here is how to keep it together.

Why AI trip plans fall apart

A real trip is several jobs. You look up flights in one chat, ask another about neighbourhoods, plan the days in a third, and work out the budget somewhere else. A week later you cannot remember which chat had the hotel shortlist, and the new chat has never heard that you are travelling with a toddler, or that you already ruled out Sunday flights.

Every time you open a new conversation, you explain the trip again — and every time, something gets left out.

Plan it once, then hand out the jobs

  1. 1
    Start a project in PassTheBrief — for example, “Lisbon long weekend”, with the dates and who is going.
  2. 2
    Press Copy the planning request and paste it into any assistant. It asks you a few questions first — budget, pace, what you love and what you would rather skip — then writes the plan.
  3. 3
    Paste its whole reply back. The plan becomes a list of tasks, each with the assistant that suits it and a ready-made prompt.
  4. 4
    Work through the tasks in whichever assistant you like. Paste each answer back, and the flights you found, the shortlist and the itinerary are saved under the right task.

What a plan looks like

For a long weekend in Lisbon, a plan might come back like this:

The plan, after pasting it back
Lisbon long weekend — 15 to 18 May, two people, about $1,800

1. Find flights that land by Friday lunchtime
   Best AI: Perplexity
2. Choose a neighbourhood to stay in
   Best AI: ChatGPT
3. Shortlist three places to stay in that area
   Best AI: Perplexity
4. Plan the three days, one area per day
   Best AI: Claude
5. Make the budget, with a buffer
   Best AI: ChatGPT
6. Book the flights and the stay
   Best AI: you

Each task comes with a ready-made prompt, so whichever AI does it
gets the dates, the budget and what you have decided so far.

When you decide something — “stay in Alfama”, “no early flights” — record it as a decision, and every assistant you hand the trip to later sees it.

A few things worth knowing

  • Check prices and opening times yourself. AI assistants can be out of date or simply wrong. Treat their answers as a strong first draft, and confirm on the airline or booking site before you pay.
  • Fix mistakes where they happened. If a later check finds the budget was added up wrong, add a correction to that task. It shows above the original work wherever the task appears, and the work itself is kept.
  • PassTheBrief does not book anything. It keeps the plan and the work; the booking is yours.

Questions

Which AI is best for planning a trip?

It depends on the job. Assistants that search the web and show their sources, such as Perplexity, suit looking things up. ChatGPT, Claude and Gemini are good at itineraries and budgets. Each task in your plan suggests one, and you can use whichever you prefer.

Can I share the plan with the people I'm travelling with?

Not yet — a notebook belongs to one person for now. You can press Pass the brief and send them the text, which includes the whole plan.

Do I need to connect an AI?

No. Copy and paste works with any assistant. If you use Claude or ChatGPT a lot, you can connect them so they read and save the plan themselves.

Does it cost anything?

No — PassTheBrief is free while it is new.

Try it with your own project

Free while PassTheBrief is new. Nothing to install — sign up with email or Google, and a short tour shows you the rest.