Which tool to choose
There's no single app that does everything well. The people who get the best results use several tools together — one for ideas, one for prices, one for verification — instead of forcing a single tool to do every job. Choose based on what's blocking you right now:
You just need to decide where to go and at what pace. Use ChatGPT or Claude. ChatGPT is still the most versatile starting point: it generates destination options, structures itineraries, explains cultural norms and prepares packing lists faster than any dedicated tool. It's free and covers most trips.
You're already on Google Maps and want stops along a route. Use Ask Maps, Google Maps' AI feature. It builds an itinerary drawing on over 300 million places, including community reviews, and it's free inside the app. Great for a road trip: ask "I'm going to the Grand Canyon, Horseshoe Bend and Coral Dunes, any recommended stops along the way?" and you get directions, estimated times and tips from real people.
You need real flight and hotel prices while you plan. Here ChatGPT isn't enough: it tends to make up prices. Use an engine that shows live results, such as KAYAK Ask AI, which pairs the conversation with up-to-date fares for flights, hotels and cars.
You want to verify that a place exists and is open. Use Perplexity: it searches with live web results and cited sources, useful for quick fact-checking.
The practical advice for non-technical users: start with free ChatGPT for the itinerary, then check every address on Google Maps. Two tools, zero cost, covers 90% of cases.
How to do it
Whether on a browser or in the app, the path is the same: open ChatGPT, paste the prompt, answer the questions it asks you.
Gather four pieces of information before writing: destination (or "not sure yet"), number of days and dates, total or daily budget, real interests (food, history, nature, nightlife, kids).
Paste this prompt, substituting your own details:
Act as a local who knows [DESTINATION] by heart, including
the less touristy spots. Plan me a [N]-day itinerary
from [start date] to [end date].
Profile: [e.g. couple in their 35s, we get around on foot and by
public transport, we love street food and museums, we hate queues].
Budget: [e.g. 120 euros per person per day, excluding hotel].
Base: lodging in the [neighborhood or "recommend the area to me"] area.
For each day give me: morning, lunch, afternoon, dinner, with
real names of places and venues, travel times on foot or
by public transport, and a cost estimate per item. Group the stops by
area so I don't waste time. Flag when a place requires
a booking. At the end, add the places you do NOT recommend and why.
- Check: if the AI gives you back a wall of generic text with no precise names or no travel times, the prompt didn't work. Reply:
Be more specific: I want exact venue names and the minutes
of travel between one stop and the next.
Refine through dialogue. Ask for concrete changes: "Day 2 is too packed, lighten it up" or "Replace the day 1 dinner with something under 25 euros." Questioning the itinerary and correcting it point by point is how it improves.
Verify every place before trusting it. Copy the venue names and search them on Google Maps: check that they exist, read the opening hours and recent reviews. This step is mandatory, not optional (see the section below).
Generate the packing list and documents. Close with an extra prompt:
Based on this trip, the season and the typical weather in
[destination] during that period, make me a packing list split
into carry-on and checked baggage. Add the documents and any
entry formalities I need to verify as an Italian citizen.
Final check: if you have a verified itinerary, bookings for the places that require them, and a packing list, you're done. Entry formalities must always be confirmed on the Italian Foreign Ministry's Viaggiare Sicuri website, not on the AI.
A concrete example
Three days in Copenhagen, a couple, mid-range budget. I paste the prompt with "couple, we love design and food, we get around by bike, 100 euros each per day excluding hotel." ChatGPT groups day 1 in the center (Nyhavn, Strøget, a dinner flagged as "needs booking"), day 2 in Christianshavn and day 3 out of town, with the minutes by bike between stops and a cost estimate per item.
The critical point comes at verification: I search the three restaurants on Google Maps. Two exist and have recent reviews; the third turns out to be permanently closed. I flag it to ChatGPT — "restaurant X is closed, give me another one in the same area and price range" — and I get an alternative that, double-checked, is open. It's the known risk: the AI suggests places that are temporarily closed or out of business, so opening days and hours must always be double-checked. Total time: 25 minutes versus the hours I'd have spent juggling browser tabs.
When it does NOT work (and how to fix it)
If the AI invents places that don't exist
This is the most serious risk. The models fabricate nonexistent places and give incorrect information; these "hallucinations" have led tourists into dangerous situations, such as travelers in Peru searching for a fictitious canyon in the Andes and a couple stranded on a mountain in Japan because of inaccurate data. Fix: before you set off, confirm places, hours, routes and safety conditions on official sources — national park sites, tourism boards, recent reviews. If a place doesn't appear on Google Maps or on an official site, treat it as invented.
If it gives you random flight and hotel prices
ChatGPT and Claude don't see live prices: they estimate them. They can tell you a flight should cost 400 euros or a hotel 150 a night, but these are indicative numbers, not offers. Fix: for real fares switch to a tool with live data (KAYAK Ask AI) or to booking sites, and use the AI itinerary only as a budget draft.
If the advice is all bland and touristy
By default AI tools stick to the beaten path. Fix: ask for it explicitly — "exclude the three most obvious attractions and give me places where the locals go" — and supplement with a human source. Forums like Reddit or TripAdvisor give up-to-date information the AI can't access.
If it asks you for card details or booking links
Watch out for scams that exploit AI. There are manipulation techniques that get systems to recommend fake booking sites. Fix: book directly with airlines and hotels, or through known agencies, and verify the legitimacy of any site before entering personal or financial data.
A tip from someone who actually uses it
Treat the AI as an enthusiastic but forgetful assistant, not a travel agency. The key is to read the output with skepticism and verify every piece of information independently: the suggestions are a springboard for research, not the final itinerary. The rule of thumb that saves me every time: no address goes into my final itinerary until I've seen it with my own eyes on Google Maps, with reviews from the last few months. Five minutes that spare you from finding yourself in front of a shuttered storefront in a neighborhood you don't know.
Frequently asked questions
Is planning a trip with ChatGPT free?
Yes, the free version of ChatGPT is enough to generate and refine a complete itinerary. Google Maps' Ask Maps is also free inside the app. You only pay if you need a very high volume of requests or the advanced features of dedicated apps.
Can I trust the hours and prices it gives me?
No, never without verification. Even specialized tools, by integrating real-time data from sources like Skyscanner and Expedia, have reduced hallucinations from 14% to 2% — but one error in twenty is enough to ruin your evening. Hours and prices must always be confirmed at the source.
What's the fastest way for a road trip?
Google Maps with Ask Maps. The feature uses map data, reviews and external sources to recommend restaurants, shops and routes, and gives you driving directions directly. Planning with Ask Maps is already widespread; some newer features, like immersive navigation, arrive first in the United States and in other regions later.
Does AI take away the fun of organizing the trip myself?
It's the most legitimate objection. For those who love the discovery phase — that time spent seeking inspiration, which is what gets you charged up before leaving — delegating everything to AI takes away the satisfaction. The middle ground that works: use AI for the boring, repetitive part (travel times, lists, grouping stops by area) and keep for yourself the part you enjoy, hunting down the little spot or the scenic viewpoint. AI should free up time for you to dream, not take it away.