Human intelligence: How to use AI to plan your holiday

The January slump is when the itch to book something usually starts. You just don’t want to spend your evenings trawling dozens of websites to make your holiday happen.

You find the perfect hotel, screenshot it, and send it to your family. But you soon check another site and find the breakfast buffet’s apparently “tragic”. Then you spot a different place, but the pool looks suspiciously small in every photo and one reviewer says it’s unheated. So you tell yourself you’ll look at the weekend. Weeks later, you start again.

If you’re facing similar battles, here are some ways AI can help sort your holiday planning.

Feed it your wish list

My partner and I have been chatting about a Greek island-hopping trip for years. It’s never happened because there are too many to choose from, and it takes serious planning. So instead of asking one-off questions, we keep everything in a single, shared ongoing chat. Each time we ask something new, it remembers what we’ve previously said.

We fed it our actual likes. Long hikes, tavern-lined towns, and long lunches that turn into late afternoons. We don’t want to pack and unpack every day. Ferries are fine, but not at 6am. We want undiscovered gems, not places ruined by Instagram.

Out of that came Amorgos and Folegandros. Islands we’ve heard of, but now added to our list. Give it enough detail, and your chatbot will stop suggesting Santorini.

When you can’t agree where to go

It’s particularly useful when nobody can agree.

A friend has two teenagers who agree on precisely nothing, a husband whose holiday happiness depends on golf, and her own hope for somewhere with great food and no self-catering. She’d been circling the same family arguments for weeks.

She fed the whole saga to ChatGPT in one go. It suggested Istria, a corner of Croatia none of them had considered, with golf courses, beaches, and excellent food. It’s not booked yet, but they’re a step away from the month of family WhatsApp arguments.

I’ve seen it work in smaller ways for staycations too. You could, say, ask for “a Center Parcs experience without the Center Parcs prices” and get a list of independent woodland lodges with hot tubs at half the cost. Someone else wanted the charm of the Amalfi Coast but less hectic, and was pointed towards Slovenia’s coast.

That’s the difference, really. A search engine needs your destination. AI can work backwards to give you ideas you might not have easily come across otherwise.

When the sums hold you up

Money is often where holiday planning stalls, because comparing your options properly is strangely exhausting.

A cheap fare from a distant airport looks tempting until you factor in the 4am taxi, the airport parking, and the stress. This is one of those moments where handing over an approximate budget helps.

Try something like: “What’s the rough cost of flying to Nice from Manchester compared with taking the train to London and flying from Gatwick, including transfers? Ask me any questions you need first.”

Once everything’s on the table, the “bargain” flight often stops looking quite so cheap. You can also ask AI to mine online forums for tips, such as recent threads on hidden gems in the Peloponnese, or flag practical concerns, like step-free access for wheelchair users.

Before you actually go

If you’re nervous about the language, try practising before you go. You can ask AI to role play a situation. One traveller I know used it before a trip to Morocco, practising how to haggle in Arabic, and while she wasn’t fluent, she was far less terrified of the souks.

And if you’re the kind of person who saves posts, itineraries and other trip inspiration, it’s worth trying Cove.ai. It’s a visual scrapbook with plenty of inspiration from fellow travellers inits gallery. You can add everything and ask AI questions, such as interesting stops on your road-trip map. Share your board with whoever you’re travelling with and add to it together.

Check the important stuff

AI’s known for confidently making things up, sometimes with video footage to match.

One elderly couple in Malaysia drove hundreds of kilometres to enjoy the Kuak Skyride cable car after watching a video online. It didn’t exist. A Spanish traveller’s trip to Puerto Rico was wrecked after relying on ChatGPT for visa guidance, which it got wrong.

So use AI for inspiration, but check official sources for the stuff that could ruin your holiday. Get that right, and there’s less faff between you and turning on your out-of-office.

Harriet Meyer has spent more than 20 years writing about personal finance before becoming somewhat obsessed with artificial intelligence

Illustration by Charlotte Durance