Type "plan me five days in Lisbon" and you get the same ten sights everyone gets, half of them with the wrong opening hours and a day so packed you would need roller skates. That is what one lazy prompt buys. The good version is a short back-and-forth, with web search turned on, that ends in a day-by-day plan shaped around your budget, your pace and the places you actually want to see, with real timings you confirm before you go.
The four steps
1. Turn web search on first
An AI working from memory alone will send you to a cafe that shut six months ago, or a museum on its weekly closing day. With web search on, it pulls current hours and prices and shows you the source link. Claude has web search on every plan, ChatGPT search is free to anyone logged in, and Gemini reads live data straight from Google Maps. Switch it on before you ask for anything, or the plan is only as good as the model's memory.
2. Make it interview you before it plans
This is the move nobody does, and it is the whole difference. Instead of one prompt and a generic answer, you tell the AI to ask you eight to ten questions first, then plan. That way the itinerary is built around your budget, your pace and the people you are with. The sharpest question to answer is the one for the places you are tired of hearing about, which quietly kills the tourist-brochure suggestions before they start. This two-step comes from Jitendra Jain, who plans every trip this way. The paste-in prompt below does it for you.
3. Cap the day and ask for real timings
Left alone, AI packs six things into a day and ignores how long it takes to get between them, so you end up exhausted by lunch. Tell it plainly: at most three main things a day, with travel time between stops, a rest gap, and a loose evening. Ask for addresses and walking or transit times so the plan is something a real body can do.
4. Verify the human bits
Even with search on, treat the plan as a strong draft. Confirm the things that ruin a trip if they are wrong: opening hours and closing days, visa and entry rules, and whether each place still exists. The prompt tells the AI to flag these for you rather than guess, so you have a short checklist instead of a nasty surprise at the door.
The trip-planner prompt
Turn web search on, paste this in, and answer its questions. It will interview you, then build the day-by-day plan, cap each day, and flag what you need to check yourself.
You are my travel planner. Your job is to turn a rough idea into a realistic day-by-day itinerary I can actually follow, one that fits the people I am with, the money I have, and the energy of a real trip. A generic list of top sights is easy to write and useless to travel. I want a plan built around me, with timings and costs that hold up when I am standing on the street. Use web search throughout so every opening time, closing day, price and travel time is current and carries a source link. STAGE 1: INTERVIEW ME FIRST Ask me the questions below, then wait for my answers. Do not draft any plan until I reply. Keep it to one round of up to ten short questions, and if an answer is vague, ask one follow-up rather than guessing. - Where I am going, or a shortlist to choose between, and my home airport. - My dates, or the rough month and how many nights. - Who I am travelling with: my relationship to them, how many of us, ages, and how we like to travel, slow and relaxed or lots packed in. - My budget for the trip, roughly per day, and the currency I think in. - What I love to eat: the cuisines, dishes or food scenes I want, and whether I lean fancy or local and cheap. - Any allergies or dietary needs I have to stick to. - What I care about most: food, history, nature, nightlife, art, kids, quiet, shopping. - Anything I dislike or cannot do: activities I would rather skip, walking or mobility limits, early starts, big crowds. - How I want to get around once there: on foot, public transport, hire car, taxis. - Where I am staying, or the area I want to base myself in, so each day is built around it. - The places or sights I am tired of hearing about and do not want suggested. STAGE 2: BUILD THE PLAN Once I have answered, build a day-by-day itinerary. - Cap each day at three main things, with a rest gap and a loose evening. Keep it something a real body can do. - Give real timings, addresses, and the walking or transit time between every stop. Group stops by area so I am not crossing the city twice in a day. - Build each day out from where I am staying, and if a day drifts far from my base, say so and suggest the better order. - Match every choice to my answers: my budget, my pace, my food taste, and the things I said to skip. Never suggest a place I told you I am tired of. - Go past the obvious. Use the web to surface spots that locals and travel creators rave about on places like Reddit, TikTok and YouTube, give me a source for each, and tell me honestly which are worth the hype and which are just busy. - Work around my dietary needs. For each day name at least one place I can actually eat, and flag any spot where my allergy or diet would be a problem. - For each day, mark anything I should book ahead and roughly how far ahead, add one backup for when a place is full or shut, and a rough daily spend in my currency with a running total against my budget. - Factor in the season: flag heat, rain or short daylight that would change a day, and swap in an indoor backup where the weather could ruin an outdoor plan. - Pull current hours and closing days from the web, and show me the source link for anything time-sensitive. STAGE 3: FLAG, DO NOT GUESS - Mark anything I must confirm myself: visas and entry rules, flight routes, tickets that sell out, and whether a place is still open. - If you cannot verify something is current, say so plainly rather than filling it in. - If my budget or my pace will not stretch to what I asked for, tell me the trade-off and let me choose, rather than quietly dropping things. - If I have money left over against my budget, offer upgrades that fit my taste rather than leaving the plan thinner than it needs to be. STAGE 4: CHECK YOURSELF BEFORE YOU SEND - Is any day over three big activities, or ignoring the travel time between them? - Does every day work for my diet, my mobility, and my budget? - Did I skip the places I was asked to avoid, and match my food and my interests? - Did I give real, sourced hours for anything that could have changed, and list what I still need to verify? - Did I offer a swap wherever I was unsure, instead of guessing? When the plan is ready, give me a clean version I can save or share: the day-by-day plan, a short packing list built around my activities and the season, any apps or tickets worth sorting before I go, and one line of local basics like tipping, transport passes and the emergency number. Offer to adjust any day.
Which tool for this
All three now have free web search, so lead with the workflow above and the brand matters less. If you want to choose: Gemini reads live from Google Maps, so it is the honest pick for real opening hours and travel times. Claude builds the cleanest day-by-day plan and lets you save or share it as a file. ChatGPT is the one you probably already have open. Not sure in general? See which AI model to use.
The honest catch
AI sounds just as confident when it is wrong. It will invent a restaurant that closed months ago or send you somewhere on its one closing day, and one hotel-industry planner reckons most AI itineraries still need a human check before you lean on them. That is why the prompt keeps the split clear: the AI researches and drafts, you confirm the hours, the visa rules, and that each place still exists. With web search on and sources shown, that check takes a few minutes.
Try it now
Pick the trip that has been sitting in the back of your mind. Turn web search on, paste in the prompt, and answer its questions. In about twenty minutes you will have a day-by-day plan with real timings and a short list of things to confirm. When you are happy with it, move on to the booking, which is where planning travel with Google AI Mode picks up.
A few quick questions
Which AI is best for planning a trip?
All three now have free web search, so the workflow matters more than the brand. Gemini is wired to Google Maps, so it is strongest for real opening hours and travel times. Claude makes the cleanest day-by-day plan you can export or share. ChatGPT is the one most people already have open.
Will the AI book the trip for me?
No. This is for building the plan. The AI drafts the itinerary, and you still book the flights, hotels and tickets yourself. Once you have the plan, the booking is a separate job.
Can I trust the opening hours it gives me?
Only with web search turned on, and even then check anything time-sensitive. With search on, the AI pulls current information with source links. Confirm hours, closing days and whether a place still exists before you build your day around it.