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
- 1Start a project in PassTheBrief — for example, “Lisbon long weekend”, with the dates and who is going.
- 2Press 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.
- 3Paste its whole reply back. The plan becomes a list of tasks, each with the assistant that suits it and a ready-made prompt.
- 4Work 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:
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 AI assistants can be out of date or simply wrong.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?
Can I share the plan with the people I'm travelling with?
Do I need to connect an AI?
Does it cost anything?
Try it with your own project
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