How AI Can Help You Plan Your Next Holiday

It’s incredible to think how far AI has come in such a short space of time. Just a year ago, I looked at dodgy images of seven-fingered people it created, and I read confidently-delivered hallucinations it wrote, and couldn’t have imagined relying on it for anything more than a laugh. But today, the tech has improved to be meaningfully useful.

That’s brilliant news for holiday planning. While there’s no replicating the human touch, and travel agents are best equipped for the job, if you’re planning your own adventures, AI tools can give you nudges and direction that would otherwise take ages to work out.

I’ve been hankering to visit Lisbon for months, so when I decided to finally make it happen, I found AI useful for so many aspects. Here’s what I learned when I used AI to plan my holiday – could it inspire your next break?

Ask it for help planning your itinerary

The natural language aspect makes itinerary planning with AI a breeze. You can say how long you have, what kind of holiday activities you’re after, and let it work its magic. It should point you to the most popular spots and ensure you don’t miss the big highlights of a destination.

It’s worth noting that if you’re after a hidden gem, you might need to research in other ways, as AI tends to give the most talked-about results for what you’re looking for.

Certainly, the way to get the best out of it is being as precise as possible. For example, on the first night in Lisbon, I knew the restaurant vibe I wanted, so I specified that, prompting ‘on the first night, find me a cosy, traditional Portuguese restaurant that’s well-rated’. You can also add dietary requirements and location preferences too.

AI can help pick areas and accommodation, but definitely cross-check its recommendations, as it can still hallucinate. For that reason, I prefer not to use AI to research flights. AI can compare airlines or explain baggage policies, but for actual bookings, stick to airline sites or third parties like Skyscanner for real-time pricing.

Once you’ve got your itinerary refined, it can help assemble it in the most useful format. Both Gemini and Claude visualise the itinerary on a map – useful for planning out your day ahead of time, and while on the move.

Let it work out all the logistics

Once the bones of the holiday are in place, it’s time to work out the details, and that’s where AI can be really useful. A simple prompt like “Now tell me the logistics around a Lisbon holiday” can reveal things like whether you need a visa, passport requirements, insurance considerations, currency, budget and ground transportation. It might even uncover things you wouldn’t have looked for. ChatGPT, for example, brought up the Lisbon City Card, which gives you free entry to major attractions and unlimited public transport.

Of course, cross-reference the really important stuff like entry requirements, and be aware that any costs it gives could be out of date. But it usually gives you a good enough sense of how to navigate the destination, even if some finer details change.

Ask it for cultural nuances

Before I go to any destination, I like to be aware of how I can be a good tourist. The problem is, it’s difficult to search for what you don’t know. Aside from obvious things like getting common terms and greetings in the native language and knowing what tipping etiquette is, it’s traditionally been difficult to tap into subtler cultural nuances as an outsider. But AI is brilliant at scanning the internet for queries like these.

I loved that Claude warned me not to take the iconic Tram 28 at peak commuter times (and it listed those times for Lisbon) so locals could use it for work, and that it’s a no-no to touch the famed azulejo tiles on buildings, as oils from hands damage them over time. That’s the kind of intel I’m after.

Use it for on-the-fly help

Ever been on holiday and wished you could have a local in your pocket to answer pressing questions? That’s where AI comes in really useful. While away, it can help with niggly things like where to go if the eatery you had planned is too busy, whether it’s safe to drink the tap water, or which open bus tour company is better.

AI translation tools are exceptionally useful too. With Google Lens, you can point it to a restaurant menu and it gives you an on-screen translation. Or with Google Translate, you can speak in your language and it translates it into theirs, and vice versa.

AI is also great when there’s an urgent situation and you’re not able to scour the internet. For example, if your flight is delayed, ask it for help and it will tell you your rights based on the flight route. Again, it needs cross-checking, but as a starter for 10, it’s the all-in-one travel tool we always needed. And looking ahead, there’s far more to come from AI.