I asked ChatGPT to plan a trek for me. Then I did it

“Can you write this again but make it funny?” I asked ChatGPT, when it spat out a detailed itinerary of a three-day hike on a section of the England Coast Path. “I want to laugh out loud while I’m reading this on the beach.”

“Day 3: A Hilariously Charming Coastal Finale,” it wrote back. It promised me a day full of “moments that would tickle my funny bone,” and then proceeded to suggest that I start my day by backtracking four miles to watch for seals at Blakeney Point, which was also on day two of the itinerary. “Step into the day with a spring in your step as you set off from Cley Next-the-Sea. The coastal path unfolds like a never-ending comedy skit, with scenic marshlands and tidal creeks providing the perfect backdrop.” 

Hilarious.

I had accepted a challenge to ask AI to plan a town-to-town trek on the English coast and then follow its orders without fact-checking—beyond confirming the existence of the places it suggested. If I’m being honest, I wanted to have a bad time. Aside from making a living from exactly the thing AI purports to do flawlessly in mere seconds threatening to render me obsolete, I am also the sort of person who still sends postcards and handwritten letters. I love off-grid nature trips and the analog ways of doing things, so, naturally, I wanted to hate this new invasion of technology into our personal lives. I wanted it to fail at planning my trip, and miserably. I daydreamt that it would try to send me hiking straight into the sea the way Michael Scott drives into a lake while following his GPS in The Office.

For better or worse, what I experienced was something much more complicated and nuanced: It’s not that AI isn’t good at planning travel. It’s just not quite there yet.

Before my trip, I spent many days conversing with ChatGPT, as well as GuideGeek, Matador’s WhatsApp-based AI travel planner (which runs on ChatGPT). When I didn’t like what one told me, I asked the other, like a child playing their parents, bending the rules to fit my own game. While these tools can spit out thousands of words in mere seconds, you have to understand exactly what to ask them in order for that output to be useful. You also have to know when it’s lying to you—which is often.

To be fair to GuideGeek—not that it has feelings, though it did apologize to me—my issue wasn’t that its suggestions were bad, just that they were poorly executed.

I thought my request was both simple and specific enough: I wanted to walk up to 45 miles of the England Coast Path over three to four days, starting and ending in towns with public transit routes to my home in London. I had a Eurail pass granting a few days of unlimited train travel, so I told ChatGPT that the cost of train tickets wasn’t an issue and that I wanted a journey of less than four hours.

I wanted AI to suggest which towns to stay in and which hotels to book there for under £100 per night, preferably with historic charm and breakfast included. I wanted it to recommend restaurants, must-do local activities, known haunts for wildlife (such as seals), and points of interest—like historic National Trust and English Heritage sites within easy walking distance of the trail (I love a good castle; who doesn’t?). Then, I wanted it to write me a cohesive itinerary with historic context notes, as if it were writing a custom guidebook just for me.

When it’s completed, the England Coast Path will be about 2,800 miles long. And unlike long trails in the United States, where I’m from, you can’t wild camp, not legally anyway. So, you have to plan out your whole trek in advance and find individual campgrounds, inns, B&Bs, or other vacation rentals for each step of the journey—many of which are not on online booking platforms that allow you to easily search a whole town’s availability on a given day. That’s what makes the prospect of a fully-functioning AI travel planner so intriguing. It’s just an awful lot of admin to plan that.

But as I say, it’s not there yet. Several times, I ended up with an itinerary that sounded fantastic, and which I was ready to book, but the links didn’t work, or the hotels didn’t exist, or the towns were in the wrong order, requiring, say, an eastward backtrack on a westward journey. Once, I noticed that it had suggested hiking between towns that are not actually connected by the trail at all.

While GuideGeek claims to search real-time availability for airline tickets and hotels, I found that it could not reliably stay within my budget parameters. I told GuideGeek what I was looking for in a hotel and it made a great suggestion, but often those places were vastly over budget and/or sold out on the dates I needed.

GuideGeek’s co-founder, Ross Borden, who is CEO of Matador, told me he’s aware of the tool’s limitations and a number of glitches. But AI is getting smarter all the time, he says—at a pace which even he finds a bit disconcerting—so these errors are a temporary nuisance. I told him that it often suggested that I backtrack, and he said that it will soon be fixed. The tool’s ability to recommend specific vacation rentals, such as an Airbnb, should be working “almost 100 percent of the time, very soon,” he says. He envisions a future in which GuideGeek gets to know you and your family and builds a profile on you, perhaps while listening to your daily conversations so that it can recommend a vacation the same way an actual trusted friend would—and then plan it for you.

Do people want that? I asked him.

Where AI has no concept of time, a human would have been able to say, “Hey, don’t cram in 15 miles that day—there are so many beautiful towns and you’ll want time to explore them.”

“I certainly do,” he said. “There’s been almost no innovation since the mid-90s in terms of how we plan, research and book trips,” he added. “AI is gonna offer an entire new renaissance to this space. And I think it will make people travel more because it’s so much easier to plan using these resources.” 

To be fair to GuideGeek—not that it has feelings, though it did apologize to me quite profusely whenever I pointed out glitches and incorrect information—my issue wasn’t that its suggestions were bad, just that they were poorly executed. On the contrary, much of my frustration came from feeling like I was rushing through something wonderful because too much was crammed into too short of a time.

I can directly compare this experience to what it’s like to have a human book it for you. A few weeks before my AI-dventure, the self-guided tour company Inntravel hosted me for a different section of the coastal path. I spent a week hiking between seaside castles in Northumberland, guided by a thick binder of trip notes compiled by someone who had personally walked the journey I was taking. While I am normally the sort of “go-go-go” person who wants to pack the miles in every day, Inntravel booked me for two-night stays in each town, so that there was time to visit the castles and take wildlife tours, rather than just speedwalk past everything.

Where AI has no concept of time, a human would have been able to say, “Hey, don’t cram in 15 miles that day—there are so many beautiful towns and you’ll want time to explore them.” A far better way to use this tool—at least for now—would be to take all the information it offers, fact-check it all, and then write your own itinerary, alongside some of your own original research.

On my last afternoon, just as I arrived in the town of Sheringham by bus (yes, I cheated; it was raining hard), I asked GuideGeek for a place in town to go for tea, ideally with “character and history and good cake.”

Even though the town has no shortage of cafes, the AI suggested I walk a “short” 30 minutes, back along the very bus route I had just taken, to the Dales Country House Hotel. I was annoyed at going so far out of the way, but the thing is, when I got there, I realized it was exactly what I wanted. I never would have chosen it if I had merely Googled “tea nearby.” And I would have missed out on a particularly delicious cake.

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