GuardTrails
Planning a trip with an AI assistant has become routine. We use one ourselves to write our itineraries. And assistants are improving fast.
But since 2025 the press has documented a series of trips that went wrong over a detail nobody had checked. None needed expertise to avoid. Each needed a check. If you design or sell tours, the list of checks is in How to check a tour itinerary.
Here are seven. Each starts from a real case, and each comes down to one action.
1. Does the place exist?
In 2025, according to a Peruvian mountain guide quoted by the BBC, two hikers were about to set off alone towards a "Sacred Canyon of Humantay". The place does not exist: the name joins two real places unrelated to the description. One of them had already paid nearly $160 to reach a remote track, without a guide, at high altitude.
The action: look up every place on a map, not in the answer. A site that appears on no map, no official site and in no recent guide is not a discovery. It is a stop sign.
2. When does the last one leave?
The same year, a couple climbed Mount Misen in Japan for the sunset, with the last cable-car time given by the assistant: 17:30. The station had already closed. They found themselves at the summit as night fell.
The action: the time of the last departure — cable car, ferry, shuttle, last bus — is checked on the operator's site, for the exact date. Timetables change with the season, and they decide when your day has to end.
3. Does this mode of transport exist?
In 2025, during a CNN Travel test of generated itineraries, an assistant suggested reaching a Hong Kong island by bus — an island that can only be reached by boat.
The action: for every leg, check that the link exists in that mode — road, ferry, train — not just that both ends exist.
4. Entry requirements
In March 2025, an Australian author learnt at the check-in desk in Mexico City that he needed a visa obtained in advance to enter Chile. He had relied on an assistant's answer, which had told him otherwise. He missed the conference he was travelling to, and told the story himself.
The action: visas, formalities, vaccinations and documents for minors are checked only with an official source: the destination country's consulate, or your own foreign ministry's travel advice. Never on the strength of an answer, a blog or a forum alone.
5. Is the address still open?
In 2024, a study of generated itineraries for major European cities found restaurants recommended with confidence that had closed for good several years earlier, and a major museum suggested during its closure for works.
The action: for every address that matters — restaurant, museum, mountain hut — check that it is recently open, and its hours on the day you will be there.
6. Driving times
This is the highest-yield check, because its errors are invisible on the page and they spread. A driving day longer than planned spills into the next one, and the whole trip slides.
The action: run every leg through a route planner, one by one. Then look at what is left of the day once the drive is taken out — especially in summer: in a desert at midday, half your walking hours disappear. See temperature ceiling and the study It isn't the north you're looking for.
7. Nights per stage
The same 2024 study found itineraries that changed hotel every night, including on two-night stays, sometimes between hotels ten minutes' walk apart.
That fault does not come from AI: it belongs to tours themselves. On the trips we took with different operators, we changed accommodation every day and a half. An assistant that learnt from the market naturally reproduces its shape.
The action: count the nights per lodging. If you change beds more often than every two days, ask why — the geometry of the route sometimes forces it, so does padding. See the study Eleven hotels in twenty nights and base-change tolerance.
What these seven checks have in common
The first five check facts: a place, a timetable, a link, a rule, an address. They take a few minutes, on official sources.
The last two check a shape: the rhythm of the trip. That is where most of the days you come back with no memory of are decided — and it is also where an operator's itinerary most often goes wrong. So they apply to any itinerary, whoever wrote it.
If you want to go further
- Tour operator, AI assistant or engine — what the first two lack is not a better answer, it is a method.
- Where to put the day with no plan — the check everyone forgets: where to breathe.
You can also send us your itinerary: we review it for free and tell you what will not hold.
Sources
- BBC Travel, "The perils of letting AI plan your next trip", September 2025 — Peru and Mount Misen cases.
- CNN Travel, test of generated itineraries for several cities, December 2025 — Hong Kong case.
- Account published by the author concerned, March 2025, and the OECD AI incidents database — Chile case.
- SEO Travel, study of generated itineraries, September 2024 — closed addresses, one hotel per night.
These cases are reviewed every six months. If they are no longer representative, they are removed, with a note in the corrections section of the Sources page.
Have a documented case missing here, or a check that saved your trip? Tell us.