3 AI Travel Planning Tools That Actually Work

AI travel tools are popping up all the time, and some of them are starting to work. Here are three we’ve tested, plus tips for how to make the most of them.

A view of the skyline of Charleston, South Carolina, with the white turret of St. Michaels Church in the foreground

We asked three AI travel tools to plan a weekend in Charleston, South Carolina.

Courtesy of Explore Charleston

I was slogging through the latest generation of artificial intelligence travel-planning tools when a stunning thing happened: I found one that pretty much did what it promised.

I was testing AI programs that purport to create instant, customized travel itineraries. Along the way I’d come across many of the hilarious, hallucinatory responses you might have read about or experienced yourself with AI tools like ChatGPT. (One sent me to an activity in Burlington, Vermont, instead of Charleston, South Carolina. Another recommended an EconoLodge as a historic hotel. And so on.)

But, against all odds and expectations, three programs proved capable of producing decent, coherent, first-draft itineraries within seconds in response to plain-language prompts: Mindtrip, Vacay, and GuideGeek.

Keep in mind, all of them produce travel plans that at best serve as outlines for you to modify and build upon. They provide some good ideas you might otherwise miss. They put a rough plan together much faster than you would using the “old fashioned” way of googling for information and searching through online booking tools.

That said, some information you get is dated, imprecise, or simply wrong. If you tried to follow the itinerary from one of these tools exactly, without checking anything before you left home, you’d wind up with a script for a Hollywood comedy: AI Family Vacation (actually that’s not a bad movie idea).

I put each of these tools to the same test: I asked them to plan a four-day visit for two to Charleston, where we wanted to eat at farm-to-table restaurants that reflect authentic South Carolina cuisine (including Gullah-Geechee food), try a couple of rum bars, and stay in a historic hotel downtown. Then I threw a curveball to see if AI could hit it: I asked it to find activities that explore the city’s obscure historic connection to the island of Barbados (the city was founded by wealthy, white Barbadian plantation owners, and their impact on Carolina culture remains).

All three basically did what they were told. They all recommended the same hotel, and some of the restaurants, nearly all good choices, overlapped too. The Gullah-Geechee and rum recommendations checked out. And while the AI tools provided well-curated lists of things to do that would introduce me to Charleston history, they mostly swung and missed at the Barbados connection.

Overall, the three tools’ performance suggest that this vastly promising, often bewildering technology can already simplify the task of planning a vacation. But it’s also not a complete solution to the age-old problem every traveler faces: figuring out how to engage with an unfamiliar part of the world, and the people who live there, in an enriching, meaningful way. Only human intelligence can accomplish that. So how did they stack up?



This tool is by far the slickest and most sophisticated of the bunch. Just type in the kind of trip you want to take, with as much detail as you can. Out comes a trip plan.

Highlights: The itinerary includes maps, so you can see how far apart things are. Each item has a live web link; hover your cursor over it and an image and summary pop up. You can view the plan as a printed itinerary or a calendar. Everything is shareable. You can ask additional questions easily and change and remove individual days. When the tool happens to recommend Mindtrip’s partners, a booking link pops up. In my case it recommended visiting Drayton Hall, a plantation built by Barbadians, and it picked the Mills House Charleston Curio Collection by Hilton, a perfectly located historic hotel, and offered a link to pick a room. (The company says partnerships do not influence itineraries, however.)

Lowlights: It hallucinated over Barbados, claiming two activities had Barbados connections when they didn’t. It incorrectly cited a Barbados connection to the City Market and sent me to a whiskey bar for rum.



This tool asks for a few specifics about your trip (destination, duration, number of people, budget), then provides two open-text fields allowing you to tell it more in plain language.

Highlights: Itineraries include per-day, per-activity, and total budget figures, and they are clearly broken down by morning, afternoon, and evening activities. Travel plans are easy to download and copy, making Vacay the best for creating printable, portable draft plans you can manually edit as Word or Google documents. It also placed me at the Mills House. It also did the best job with Barbados, recommending a visit to the Charles Towne Landing state historic site, where the Barbadians landed in 1670, and the International African American Museum, which includes displays that explain how Barbados and Charleston are linked to the African diaspora.

Lowlights: The plans from Vacay lack maps and web links. To modify the itinerary, you can query again or consult with the Vacay chatbot, but those additional answers don’t update your original itinerary.



Created by the travel media brand Matador, GuideGeek is a chatbot available via Facebook, Instagram, and WhatsApp. Send an instant message to GuideGeek to get going, then input your requests as text. Out comes a plan.

Highlights: As a chatbot, GuideGeek invites continued conversation so you can ask for details, tweaks, and elaborations. It will provide live web links on request, though some are dated or broken. I found this to be the easiest pocket AI travel consultant. It also placed me at the Mills House!

Lowlights: GuideGeek works only on mobile devices. Itineraries are broken into arbitrary chunks based on the message length allowed by each platform, so the whole thing isn’t easy to download or copy. GuideGeek seriously whiffed on the Barbados connection; it recommended four activities that had nothing to do with it, and sent me to a contemporary distillery that doesn’t make rum.

Three tips for planning a trip on AI

Be very specific. All generative AI tools work better when you give them very detailed directions. Broad requests about a trip generate information drawn largely from the first page of Google search results.

Don’t like it? Change it. Once you have your itinerary, you can ask to update, dig deeper, or create another version.

Two (or three) neural networks are better than one. Use multiple tools to check the others’ work. Mix and match, verify all the information, and add your own knowledge and research from real humans you trust.

Craig Stoltz
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