How to Use AI for Travel Planning Without Ending Up With Generic Itineraries

The first time I tried planning a trip with ChatGPT, it gave me a 5-day Tokyo itinerary that suggested visiting Senso-ji Temple, eating ramen in Shinjuku, and "exploring Shibuya Crossing." Useful if you've never opened a guidebook. Useless if you've ever read one.

The tools can help. People just use them wrong. They ask for "a 7-day itinerary for Italy" and get back the median internet opinion of what Italy is. To get anything better, you have to feed the model constraints, taste, and friction points. This is how I do it.

Skip the "plan my whole trip" prompt

This is the single biggest mistake. Asking ChatGPT or Claude to plan your trip end-to-end gives you a hallucinated mashup of the top 10 TripAdvisor lists for that destination. The model has no idea what you actually like, how you move through a city, or how tired you'll be on day three.

Use AI as a research assistant, not a tour guide. The model is excellent at narrowing options, comparing trade-offs, and surfacing things you wouldn't have searched for. It is bad at building a real schedule.

Front-load your constraints

Before you ask anything, write a paragraph of constraints into the chat. Mine usually looks like this: "Mid-30s couple, traveling Oct 15-22. Lisbon based. We hate buffet breakfasts, we walk a lot, we don't drive abroad, we'd rather pay $40 for a great meal than $200 for a famous one. We've been to Barcelona, Rome, and Madrid, so don't suggest anything that overlaps. We get one Michelin meal as the budget anchor."

That paragraph is worth more than every prompt-engineering tip you'll read this year. The model now knows what to filter out. Without it, you get the average tourist trip.

Ask the right kind of question

Bad: "What should we do in Lisbon?"

Better: "What's a half-day in Lisbon that wouldn't show up in a typical guidebook, given we already plan to do Alfama and Belem?"

Even better: "Compare Sintra, Evora, and Setubal as day trips from Lisbon for someone who's already been to wine country in Tuscany and isn't impressed by castle exteriors."

Comparative questions are where AI shines. Open-ended questions are where it hallucinates. If you find yourself getting generic answers, your question was generic.

Use Perplexity and Claude differently

I use these tools for different parts of the trip. Perplexity is better when the answer requires a current source: flight rules, visa requirements, opening hours, whether a restaurant is open on Mondays. It cites sources, and the sources are usually correct.

Claude is better when the answer requires synthesis: building a packing list from a forecast, drafting an itinerary outline once I've made the major decisions, translating rough notes into a clean shareable doc for whoever I'm traveling with. ChatGPT sits in the middle and is the most likely to invent a restaurant that closed in 2019.

For actual booking, none of them are good. Use a real flight search like Google Flights or Kiwi, and book restaurants directly through their site or through Resy. The "I'll just have the AI book it" workflow is two years from being reliable and currently a fast way to get scammed.

Verify three things before you trust anything

Three categories of AI travel hallucinations have cost me time.

Restaurant addresses and hours. I've been routed to dead storefronts twice. Cross-check on Google Maps with a review from the last 60 days.

Transit details. Models are confident about train schedules they made up. Use the operator's site (Trenitalia, JR East, Renfe) for anything time-sensitive.

Visa and entry rules. These change. Check the official government site, then the airline's confirmation. AI is fine as a starting point for "do I need a visa for X as a Y passport," never as the final answer.

If you'd be unhappy missing it, verify it. Everything else, let the model guess.

A workflow that actually works

The version I've landed on after five or six trips: Dump constraints into a chat with Claude. Ask it to summarize what I told it back to me so I can correct misreadings. Ask for three or four candidate days, not a full itinerary. Pick one. Ask Perplexity to verify opening hours and surface anything time-sensitive: festivals, closures, ticket pre-booking. Build the final shape myself, in a Google Doc, with the AI's research as raw material rather than the plan.

Total time: maybe two hours for a week-long trip, versus the eight or so I used to spend on guidebooks and forums. The trip is better, too, because the constraint paragraph forces me to figure out what I actually want before I start looking.

Stress-test before you go

Once you've planned the trip, paste the final itinerary back into Claude and ask: "What's wrong with this? What am I missing? What would a local roll their eyes at?" The pushback is usually worth more than any single recommendation in the original plan.

Next on my list: how to use AI for trip recovery, for the moment when flights cancel and reservations vanish and it's 9pm in a city you don't speak the language in. The model is shockingly good at that part.