Planning a trip with AI — and checking it before you book

Planning a trip used to mean a pile of guidebooks and a dozen browser tabs. Now you can describe what you’d like — “a gentle week in Portugal in May, not too much walking, good food, one or two day trips” — and get a full outline back in a minute.

It’s one of the best everyday uses of AI. It’s also the one where a confident wrong answer costs real money. So here’s how to get the good part without the expensive part.

What AI is excellent at

The shape of a trip. “Five days in Vienna for two people in their sixties who like music and cafés” gets you a sensible day-by-day plan: which neighbourhoods, which sights are near each other, where a rest day fits. This is the tedious part of planning, and AI does it in seconds.

Answering the questions you’d be embarrassed to ask. “Is it rude to tip in Japan?” “Do I need an adapter for Italian sockets?” “How do you pronounce ‘Bruges’?” It’s patient, it doesn’t judge, and it’s usually right about things millions of travellers have asked before.

Comparing options. “Train or coach from Edinburgh to Inverness — which is more comfortable for someone with a bad hip?” It’ll lay out the trade-offs clearly.

Packing lists. Tell it where, when, how long, and anything special (walking poles, medication, a wedding). You’ll get a list to tick off.

Drafting the awkward emails. “Write to the hotel asking for a ground-floor room because of my knee.” (See writing a difficult email.)

What AI is bad at — and this is the important bit

Anything with a number or a time. Opening hours, prices, train times, whether a museum is closed on Mondays. The AI’s knowledge has a cut-off date, and even before that, it’s working from patterns, not a timetable. It will state “the museum opens at 9” with total confidence and be wrong. Every time, every number: check the official website.

Whether something still exists. Restaurants close. Hotels change hands. Ferry routes get cancelled. AI will happily recommend a café that shut in 2022.

Availability and booking. It cannot see whether a hotel has rooms on your dates. If it says “book the Hotel Bella Vista,” that’s a suggestion, not a reservation, and not a promise that it’s any good today.

Specific travel rules. Visa requirements, what you can carry in hand luggage, whether your passport needs six months’ validity. These change and they matter. Use the official government travel site for your country — it exists precisely for this.

The method: plan with AI, verify with the source, book with a human-facing site

Here’s the routine that keeps you safe:

1. Sketch with AI. Describe the trip. Get the outline. Ask follow-ups. Enjoy this part — it’s fun.

2. Ask it to list what needs checking. Literally: “Which parts of this plan should I verify before booking?” It’s good at flagging its own weak spots — it’ll tell you to check the ferry times and the museum days.

3. Check each one at the source. The museum’s own website. The railway’s own timetable. Your government’s travel advice page. Ten minutes, and you’ve turned a nice-sounding plan into a real one.

4. Book on sites you’d have used anyway. Your usual booking site, the airline directly, the hotel directly. Never through a link the AI gives you — links in AI answers can be out of date or, in rare cases, wrong altogether.

A worked example

You type: “Plan a relaxed four-day trip to Copenhagen for two people in our late sixties, in September. We like gardens, good coffee, and we don’t want to walk more than a couple of miles a day. One day trip would be nice.”

It gives you: a day-by-day plan — Tivoli and the harbour on day one, the botanical garden and a café district on day two, a day trip to a castle by train on day three, a gentle last day. Sensible, well-grouped, and a good starting point.

You then check: Is Tivoli open in September? (Its website says yes, but hours vary — noted.) Which train goes to the castle, and how often? (Railway site.) Is the botanical garden’s glasshouse open? (Its own page says it’s closed for repairs — good thing you looked.)

You then ask the AI: “The glasshouse is closed. What’s a similar gentle alternative for that morning?” And it adjusts.

That’s the relationship: it plans, you verify, it adjusts. Nobody’s paid for a closed glasshouse.

Two small extras worth knowing

• Ask for accessibility explicitly. “Which of these have steps?” “Is there seating?” It’ll often know, and it’ll remind you to confirm.
• Ask it to make you a checklist for the day before you leave. Passport, chargers, medication, a printed copy of bookings. The dull stuff it’s good at.

The one thing to remember

AI is a superb planning partner and an unreliable source. Let it do the thinking; do the checking yourself, at the real website, before any money changes hands.