What you’ll be able to do

By the end of this, you’ll be able to give an AI assistant the basic facts about your trip, dates, budget, who’s coming, how you like to travel, and get back a proper day-by-day plan. Opening hours, travel times between stops, a rough sense of what things cost. Not a finished itinerary you can trust blindly, but a really solid first draft that would’ve taken you an evening of tab-switching to build yourself.

The plan won’t be perfect. That’s fine. You’re not outsourcing the trip, you’re outsourcing the boring bit of pulling it all together.

Before you start

Here’s the thing you need to know before any of this works: AI tools are good at structure and genuinely bad at facts that change over time. Ask ChatGPT, Claude, Gemini or Perplexity to plan three days in Lisbon and you’ll get a sensible-looking itinerary with named restaurants, museum hours, and neat little time blocks. Some of that will be right. Some of it will be confidently, plausibly wrong, an opening time that changed last year, a restaurant that closed, a “hidden gem” that’s been on every listicle since 2019.

This isn’t a reason to avoid using AI for trip planning. It’s a reason to treat the output as a draft written by someone who’s read a lot about your destination but hasn’t actually been there recently. You still check everything. Especially anything involving money or a booking.

Perplexity is worth a mention here because it tends to show its sources, which makes checking easier. Gemini can pull in information from Google Maps, Flights and Hotels, which helps with logistics. But none of them are reliably up to date on the small stuff, opening hours, ticket prices, whether that restaurant is still trading. Treat every specific fact as something to verify, not something to trust.

Get set up

You don’t need anything fancy. A free account with ChatGPT, Claude or Gemini will do the basic itinerary-building job fine. If you want something built specifically for trip planning rather than a general chatbot, Mindtrip, Layla and Wanderlog are all AI trip planners designed around exactly this, with maps and itinerary layouts baked in rather than plain text you have to reformat yourself.

For the logistics side, once you’ve got a rough plan, Google Maps and Rome2Rio are useful for checking actual travel times between places, which AI tools often estimate rather than pull from anywhere reliable.

Before you write your first prompt, gather:

Your dates, exact ones, not “sometime in June.” Your budget, roughly, and whether that’s per person or total. Who’s travelling, ages if kids are involved, mobility needs if relevant. Your pace, do you want three activities a day or one long lazy one. What you hate. This one matters more than people think. If you can’t stand queuing, say so. If you loathe walking tours, say so. The AI can’t guess your preferences, it can only work with what you give it.

Have all that written down somewhere, even just a note on your phone, before you start typing.

Try it yourself

Here are three prompts that each do a different job. Copy them, swap in your own details, and see what comes back.

The first is your basic itinerary request:

I'm planning a trip to Lisbon for 4 nights, arriving Thursday 12 June
and leaving Monday 16 June. It's me and my partner, mid-30s, budget
around £150 a day total for food and activities (not including
accommodation). We like a relaxed pace, no more than two activities
a day, and we hate anything touristy or crowded. We love good food,
walking, and small local bars. Give me a day-by-day plan with
suggested times, and flag anything I should double check for opening
hours or closures.

The second narrows in on activities once you’ve got the shape of the trip:

For day 2 of my Lisbon itinerary, suggest three alternative
afternoon activities that aren't the usual tourist spots. I want
something with a local feel, ideally involving food or a market.
Tell me what's nearby so I can pair it with dinner.

The third is about the logistics, the bit that’s easy to get wrong:

Here's my rough itinerary for Lisbon: [paste your plan]. Can you
estimate travel time between each stop, and tell me if any of the
days look too packed or involve a lot of backtracking? Also tell
me what's typically closed on Mondays in Lisbon, since one of my
days is a Monday.

Three different jobs: the overview, the detail, the logistics check. Run all three and you’ll have something worth working with.

Check the result

Right, this is the part people skip and shouldn’t. Once you’ve got a plan back, run these checks before you book anything.

Pick two or three specific claims, an opening time, a restaurant name, a ticket price, and search for them independently. Go to the venue’s own website or its official social media. If the AI says a museum is open until 6pm on Sundays, check that against the museum’s actual site. It takes two minutes and it’s the single most useful thing you can do.

Ask the AI directly where it got a fact from. Something like “where did you get that opening time from?” Sometimes it’ll tell you it’s not certain, which is useful information in itself. If it can’t point to anything solid, treat that fact as unverified.

Cross-check travel times against Google Maps or Rome2Rio. AI-generated itineraries have a habit of underestimating how long things take, especially if it’s suggesting you nip across a city between two activities that are actually forty minutes apart.

Look out for restaurant names that sound suspiciously perfect, “the best pasteis de nata in Lisbon”, that kind of phrasing. That’s often a sign the AI is repeating something from an old article rather than checking anything current. Search the name plus the city and see if it still exists and still has decent recent reviews.

And ask what’s closed on your specific dates. Public holidays, Mondays for museums, siesta hours, these get missed a lot. If you’re travelling around a bank holiday, ask explicitly, don’t assume the plan has accounted for it.

If it doesn’t work

Sometimes the plan you get back is vague, generic, or just doesn’t fit. Usually that’s a prompt problem, not a tool problem.

If the itinerary feels like it could be for anyone, going anywhere, you probably didn’t give it enough to work with. Go back and add the specifics: your actual budget, what you hate, how much walking you’re happy with. The more concrete you are, the more useful the output.

If it keeps suggesting things that are closed, too expensive, or nowhere near each other, say so directly and ask it to try again with that constraint. “That restaurant is £80 a head, I said budget, try again” works better than starting from scratch.

If you paste in a rough draft itinerary and ask for changes, sometimes it loses track of earlier details, your budget, your dates. Just restate them. It’s not insulted, it’s not going to remember unless you remind it.

Now the bit that matters more than any of that: never hand an AI tool your passport number, your card details, your booking reference numbers, or anything that could be used to access your accounts. There’s no version of “plan my trip” that requires that information, and typing it into a chat window doesn’t make it more private just because you’re asking politely. If a prompt or a tool asks you to paste in personal documents to “personalise” your itinerary, don’t.

Keep your actual bookings, confirmations, and payment details somewhere else entirely. Use the AI for the planning, do the booking yourself, on the venue’s own site.

Keep exploring

If you’re already deep into planning, a few other guides on this site pair well with this one. “How to get AI to translate a live conversation” is worth a look if you’re heading somewhere you don’t speak the language. “How to get AI to make a playlist” is a nice one for the actual journey, road trip or long flight. And if you haven’t booked accommodation yet, “How to get AI to compare products before I buy” covers a similar checking process, just applied to hotels rather than restaurants.

Sources and review notes

Review date: 15 September 2026 — every source above was opened and checked against the text on that date.