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Travel Planning With AI: I Tested It for a City I Know Inside and Out

Would you let AI plan your next vacation? For the time-poor among us, it’s a tempting proposition.
There’s no two ways about it — planning a great trip is a labor-intensive activity. If you’re not careful, you can spend as long reading about and preparing to visit your chosen destination as you’ll eventually spend on the ground there. And with many major tourist cities attracting more visitors than ever, even the most seat-of-their-pants kinds of traveler needs to do some preparation.
Over the past year, generative AI (in which you use a prompt to ask an algorithm to generate content — either text, image or video) has become a publicly available plaything, leading it to be touted as a promising, if often over-hyped, tool to be used in almost any context you can think of. No surprise then that as the world has experimented with OpenAI’s ChatGPT tool, many people have been using it to quickly and efficiently create travel itineraries.
A number of travel-specific AI services have sprung up as a result, offering to take on the burden of generating itineraries. But are they any good? Results have been mixed, suggesting there’s no black-and-white answer to this question. It’s not so much whether you should use AI to plan an itinerary, but how to use it to achieve the best results.
As someone who lists trip planning as a top-three hobby, I was keen to explore its potential and its limits.
I decided the best methodology would be to use my own city of Edinburgh as a testbed for a three-day trip. I know Edinburgh like the back of my hand, it’s a popular destination and it’s the ideal location for a quick getaway, even from the US. It’s small enough that you won’t leave feeling as though you’ve barely scratched the surface, but big enough and packed with history and tourist attractions so that there’s no chance of you finding yourself at a loose end by Sunday afternoon.
I used a range of AI travel tools to build itineraries including ChatGPT, GuideGeek, Roam Around, Wonderplan, Tripnotes and the Out of Office, or OOO app. Here’s how I got on.
Travel itineraries: An art, not a science
A well-constructed travel itinerary is more than just a list of attractions, neighborhoods and local businesses. The best itineraries will string your day together in a way that makes sense geographically and thematically.
The journey between attraction A and attraction B will be part of the fun, taking you down a picturesque street or providing a surprising view you might not otherwise have seen. It will also be well paced, taking into account that by the third gallery of the day, even the most cultured among us will likely be struggling with museum fatigue.
Very few of the itineraries I asked AI to create for Edinburgh fit this brief. Roam Around, Tripnotes, OOO and Wonderplan clearly had no sense of the geography of the city. ChatGPT and GuideGeek did a much better job of grouping attractions according to neighborhood, building a day around Edinburgh’s Old Town, a day around Holyrood and Arthur’s Seat, and a day around the New Town area.
The most egregious examples of nonsensical itinerary planning came from OOO and Roam Around when I tested them further by asking them to create larger itineraries for a seven-day trip around Scotland. Roam Around presented me with a fantastic selection of activities and attractions around the country but suggested I drive hours back and forth to Edinburgh for every meal.
Meanwhile, Day 1 from OOO started me off with breakfast and a graveyard in Edinburgh, a Glasgow Museum at lunchtime, Glenfinnan Viaduct in the Highlands in the afternoon, before staying overnight at a hotel on the Isle of Skye (but with drinks and dinner back in Edinburgh). That’s 10 and a half hours of driving, and it only got more exhausting from there.
I approved of the majority of the suggestions AI came up with for Edinburgh, and for Scotland more broadly, both in terms of attractions and local businesses. But aside from ChatGPT and GuideGeek, which were able to create thematically and geographically cohesive itineraries when pushed, the way they were strung together was often counterintuitive.
It’s clear that many AI tools are doing little more than aggregating information found elsewhere — an approach that leaves you with what Lonely Planet Senior Editor Laura Motta describes as

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