Could your next holiday be planned by artificial intelligence (AI)? More and more people are choosing to use tools like ChatGPT, Vacay and GuideGeek to cut down booking time and cost when deciding the details of their next trip.  

AI trip planners can be quick, convenient and easy to use with itineraries often generated in seconds. These can then be customised as much as you like, depending on what details you feed into the planner. 

Omio’s 2024 NowNext travel report highlighted that 44 per cent of European and US travellers revealed that they would use AI to book and plan travel this year, which was up from 27 per cent last year. 

According to Gen Z and millennial travellers surveyed by American Express, some of the most useful travel features of generative AI were budgeting and expense management, activity recommendations, personalised trip recommendations and translation help. 

With all of this in mind, my growing curiosity got the better of me. I decided to let AI plan my early March trip to Tallinn, Estonia with my husband. 

AI can make your trip planning lightning-fast

Given ChatGPT’s overwhelming popularity, I used it to plan the bulk of my trip. However, I also tried out Vacay and GuideGeek, just to have something to compare ChatGPT’s recommendations to. 

We’d already booked the hotel, so I asked the tools to plan a three-day, two-night budget trip. All three platforms suggested very similar itineraries, with only slight differences in restaurants, activities and timing. This was done in seconds, cutting down on weeks of time-consuming, confusing and contradictory research. 

ChatGPT’s version was the most comprehensive and interesting to me. It included classic attractions such as Tallinn’s Old Town, the Alexander Nevsky Cathedral, Kiek in de Kök and Bastion Passages Museum, Kadriorg Park and Palace, the Balti Jaam market and more. 

We used many of the recommendations while actually in Tallinn. I especially enjoyed Kiek in de Kök, which is a fascinating defensive tower, part of a larger museum complex, as well as Kadriorg Park, where we could make the best of the crisp early March weather. Balti Jaam market had some great food options and a vast collection of historical and quirky handicrafts.

I also liked that all the tools mostly captured the essence of Tallinn, suggesting attractions and activities most representative of the city. 

Estonia’s oldest cafe, Cafe Maiasmokk turned out to be a desert heaven with beautiful decor. Another popular chain, Cafe Reval, also had a vast menu and a sleek, modern vibe, perfect for lingering over a cup of matcha. 

AI travel tools can be outdated and glitchy

One of the biggest issues we had on this trip was food. While I eat mostly everything but don’t particularly like beef or other red meat, my husband does not eat fish or red meat. 

Neither of us is very fond of pancakes either, and although we’re foodies, we’re not very adventurous eaters. This left us in a bit of a pickle, as most of the initial ChatGPT recommendations for restaurants leaned heavily towards traditional Estonian foods, such as a variety of pancakes and elk meat. Vacay and GuideGeek did the same too. 

I had to narrow down our criteria several times, such as asking for restaurants with more chicken options, or certain types of cuisine specifically, until ChatGPT provided more suitable options. 

However, each time I repeated the process, the overall itinerary seemed to become worse and worse, with a drastic drop in the number of activities or places to visit. 

The information was often outdated too. Much to our dismay, some restaurants were permanently closed like Restaurant Vanaema and Juures and Kohvic Komeet. Something which we only found out when we were starving and looking for a place to eat. 

Other suggestions, like Cafe Nop, was more like a health food store, with hardly any breakfast choices. This was also a problem with Cafe Rost, which had a very famous cinnamon bun, but very little else. 

Is booking a trip using AI worth it?

For me, the amount of input details, like fitness levels and type of holiday required to get a good AI plan was a slight drawback. Especially given one of the benefits of using tools like these is supposed to be less time spent on planning. 

I am not the only one to have experienced problems with outdated data either.  

“I had clients who nearly booked a sakura-themed trip to Kyoto based on AI suggestions, completely unaware that cherry blossom seasons have shifted due to climate change and that many temples now require advance reservations due to overtourism policies put in place just last year,” says travel advisor and writer Coco Tran. 

She highlights that AI can’t replace real, on the ground experience either. 

“AI simply can’t provide real-time insights about travel’s constantly changing conditions. It processes data, but can’t tell you which Japanese ryokan genuinely welcomes foreign guests versus those that merely tolerate them – nuances I’ve learned through years of relationship building.”

My final thoughts? You should definitely use AI trip planners to give you a rough itinerary, but nothing beats your own research.

If you are going to give it a try, double-check the details, cross reference the AI suggestions and customise the initial plans you are given.