How to plan a trip with AI

By the end of this, you will have a day-by-day trip itinerary shaped around your budget, your interests, and the people you are travelling with, ready to refine and book.

What you will need

• Any AI chat tool: Claude, ChatGPT, or Gemini all work well.
• The basics of your trip: where, when, for how long, and who is coming.
• About 20 to 30 minutes.

Step 1: Brief the AI on your trip

Start by giving the AI the full picture. The more it knows about your budget, your pace, and what you enjoy, the more the plan will suit you rather than a generic tourist.

Help me plan a trip. Here are the details:

- Where: [destination]
- When and how long: [dates, number of days]
- Who's going: [e.g. two adults and a seven-year-old]
- Budget: [rough total or daily spend]
- What we love: [e.g. food, museums, slow mornings, being outdoors]
- What we'd rather avoid: [e.g. long queues, early starts]

Please don't write the plan yet. First, ask me anything that would help you
tailor it.

What to expect: the AI will ask a few clarifying questions, perhaps about how much you like to pack into a day. Answering them makes the itinerary far more personal.

If it does not work: if it jumps straight to a plan, reply with “Please ask your questions first before drafting anything.”

Step 2: Get a day-by-day itinerary

Now ask for the plan itself. Being specific about structure keeps it realistic and easy to follow.

Now draft a day-by-day itinerary for the whole trip. For each day, suggest a
morning, afternoon, and evening, keep the pace relaxed, and group nearby things
together so we're not criss-crossing the city. Add a rough cost estimate for
each day.

What to expect: a clear plan broken down by day and time of day, with costs attached. Read it as a starting point, not a fixed schedule.

If it does not work: if a day feels too packed or too empty, say “Day three is too busy for us, please spread it out,” and it will rebalance.

Step 3: Refine it to fit real life

Travel plans rarely survive first contact with reality, so shape the draft around your actual constraints now.

Adjust the plan for these: we want one completely free day with nothing booked,
we'd like a sit-down dinner on our last night, and we're travelling by public
transport, so please keep that in mind when you suggest what to do each day.

What to expect: an updated itinerary that respects your constraints. Keep tweaking with follow-up messages until it feels like a trip you would actually enjoy.

If it does not work: if it forgets an earlier request, restate it briefly. Repeating a key detail is normal and quickly gets you back on track.

Step 4: Check the important details

This step matters, so do not skip it. AI can confidently suggest a restaurant that has closed or opening hours that have changed, so verify anything you plan to rely on.

List every specific place, opening time, and price you've mentioned in this
plan. Mark which of these I should double-check myself before booking or
turning up.

What to expect: a checklist of the details worth confirming. Look up the key ones, opening hours, prices, and whether anything needs booking ahead, using official websites or a maps app.

Wrapping up

You now have a personalised, realistic itinerary and a short list of things to confirm before you go. From here you can ask the AI to build a packing list, suggest a few phrases in the local language, or draft a simpler one-page version to carry with you on the day.

A tip before you book: treat the AI’s plan as a knowledgeable friend’s suggestions, not a booking service. It does not have live access to prices or availability, so always confirm the details on the day you travel.