Everyone who travels knows this very particular feeling. You already know your destination and roughly how many days you are planning to stay there, but you don’t have a precise plan for it. So, you turn to ChatGPT and type your query. The AI provides you with an entire travel schedule, including hotels, daily activities, places to eat, and modes of transport. Looks great. Looks like all covered.
But it works just too well to be true. And herein lies the trouble.
In the past year, actual events started repeating themselves. In August 2025, a Spanish travel influencer, Mery Caldass, asked ChatGPT if she needed special documents to fly from Spain to Puerto Rico. The AI told her that she did not need anything. However, the problem with this answer was that Puerto Rico, being a territory of the USA, required her European citizenship to be granted ESTA authorization. Thus, she was stopped by the security guards at the airport gate and denied boarding. Her video, which shows her standing there in disbelief, went viral on TikTok.
The surprising element in the whole story is not the error. It is the way in which the AI gives out that error. Very confidently, no “I think so” or “check if this is true.” Just the answer. Which is wrong and leaves you with a ticket that doesn’t work anymore.
In other words, it is not about the question of whether the AI assists with your travel plans. Of course, it does. The question is at what point it fails and what information needs to be confirmed.
THE DATA STOPS. THE WORLD KEEPS MOVING.
Every AI model is built based on information up until a certain cutoff point. Beyond that point, the world changes in ways the AI does not see. An attraction that closed down at the end of 2023 may still show up in a recommended itinerary generated by the AI in 2026, while an establishment whose praises were sung in numerous articles three years ago may already have long since closed its doors, and the AI has absolutely no clue about it.
Travel safety researchers have established that over 50% of all recommendations generated by AI models take the traveler to attractions that are beyond their operational hours, while nearly a quarter of the suggestions are for establishments which do not exist anymore, being either permanently or temporarily out of business. A study conducted early in 2026 showed that all eight major AI itinerary generators needed to be checked manually.
According to AFAR, one of their travelers used AI to make a plan for circumnavigation of the lake. In this case, AI made a routing right. But later AI planned a day of drive, which was technically impossible within the hours provided. The distance was off. There was no possibility to differentiate between the two by the app itself.
This issue can be addressed easily, without much effort. First, before booking or scheduling anything, from eating in some restaurant, visiting museums, or other attractions, just take a moment to check their working schedule via Google Maps and websites of those places.
VISA REQUIREMENTS ARE NOT WHAT YOU SHOULD TAKE CHANCES ON
The problem faced by Mery Caldass wasn’t isolated. In the same era, there were incidents where an Australian citizen had become stuck in Mexico City because of a bot giving him inaccurate visa information regarding entry into Chile with an Australian passport. The chatbot gave him this info very confidently. However, the info was incorrect.
Requirements for a visa may vary from time to time. There may be new systems introduced for authorizing entry. Conditions for entry can become stringent as per mutual agreements between nations, and these may not find mention in an AI training dataset. As pointed out by a travel insurance company called Faye, most of the time, an AI system is fed incomplete data that may not even be correct at all.
When it comes to any questions concerning your ability to travel by air or enter another country, the most trustworthy sources are the official website of the country where you plan to travel. Always refer to the official immigration or consulate websites, especially if your travel plans are non-refundable.
THE PERFECT ITINERARY ON YOUR DISPLAY
While it is quite bad with regards to physical distance, actual traffic situation, and the experience of traveling from one point to another in an unknown city, it can generate a perfect itinerary that looks neatly planned when you ask it to create a plan for three stops. However, it does not know about the fact that two out of three stops take ninety minutes by car in rush hours, which the bus line assumed to be operating was no longer available, and that a walk considered to be short is actually done on a steep slope and very tiring for almost everyone.
It is perhaps one of the most commonly mentioned complaints of travelers who used AI-generated itineraries.
Make your way through Google Maps. Make sure that you check the estimated time based on the exact time that you would travel on the day you choose, rather than a general estimate. Be aware of the expected waiting time at each destination if you know it takes forever to get past the queue at weekends. AI will not be able to do this, and over-planning guarantees a stressful trip.
THE PLAN WAS CREATED FOR NO ONE IN PARTICULAR
Since you are not explicitly mentioning your own specific details, AI creates an itinerary for some imaginary traveler. This traveler is not limited by any budgetary restrictions, any physical considerations, pace preferences, and any particular interest in traveling at all.
If you have four days and need one of them for almost nothing, AI will make sure that this day is filled somehow. If you are moving slowly or easily exhausted, the itinerary will be designed as if neither were your case. And if you are traveling with kids, AI can suggest the same itinerary for an adult couple on a honeymoon.
This was highlighted well in an analysis from 2025 regarding the use of AI-based travel planning tools. If the prompts are very general, then the response will inevitably be very general as well. Assumptions made by AI in filling gaps are bound to be incorrect on behalf of the particular individual.
Write down your situation before prompting for a plan. The amount of money you will spend each day. Your speed when traveling. The sights you are really excited about seeing and the ones that do not matter so much to you.
HOW AI DESERVES ITS PLACE
None of this is to say that AI is an inappropriate choice when it comes to making travel plans. AI works well in terms of bringing out new ideas fast, putting similar places close together, allowing comparison between options in different cities, and reducing research time from hours to half an hour. That makes it pretty useful.
The problem occurs when you treat AI’s suggestions as final recommendations. The best way to describe AI’s role in this case would be a collaboration with an intelligent assistant who knows a lot about travels but has not seen the destination in person in the last couple years.
Use the information provided by AI as a guide. Then validate your information using live sources. Validate the travel time from actual maps. Verify the visa requirements using official websites. Find out whether places are still operational.Most of the work has been done by AI for you. However, it is in the later stages that the actual planning begins.
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