New AI tool can help you plan your itinerary

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Artificial intelligence software and the new wave of chatbots that run on it have quickly taken over everything from stock markets to the national news narrative. Next up: Your holiday planning.

There’s a new, AI-powered website called which will spit out a detailed itinerary of what to see and do on your next trip – and in our initial experience, some of the ideas are pretty good. Just plug in your destination, when you’ll be visiting, and how long you’ll be staying. Fifteen seconds or so after hitting Enter, you have a day-by-day itinerary filled with where to go when, places to eat and more.

roam around io

It’s among the first travel-focused applications we’ve seen to use this vibrant new technology. And while it’s called, it’s actually powered by ChatGPT—the now-famous chatbot that practically paved the way for this AI explosion.

Who is behind this tool? We do not know. Internet registration records from the site have been redacted for privacy – all we know is that the site was originally created sometime in February 2023.

A word of caution: All of these AI tools are a product of what’s already on the internet… and we all know it’s not perfect. Travelers will want to double-check for errors and off-base suggestions before plowing ahead with a itinerary. Think of it as a starting point for planning your trip, not a tailor-made itinerary you should follow to a T.

Here’s a closer look at how it works.

How to use

Getting started with couldn’t be easier.

Just go to and enter the details of a trip you’re planning: Where you’re going, when your trip starts and how many days you’ll be visiting. Press Enter and in 15 to 30 seconds it will give you a day-by-day itinerary with suggestions for sights to see, restaurants to eat, day trips to do, and more.

But is it any good? To put to the test, I connected to some cities I’m familiar with to see what it came up with. Are the lunch or dinner recommendations good? Do the suggestions make sense? Does it even identify the right city?

For example, I recently returned from a short two-day stay in Tokyo and saw as much of the city as I could. I thought I could be a decent judge of whether Roamaround’s suggested itinerary was solid or stupid.

Here’s what it came up with:

roamaround tokyo itinerary

My verdict? Not bad! Roamaround clearly understands geography, as it does not advise you to jump from one place to another that is miles away. For example, it’s only a five-minute walk or so from Tokyo Tower to Zozoji Temple, and the alleys of Golden Gai are actually in Shinjuku. The selection of expensive versus modest meal suggestions is a nice touch, although you could argue that some of the restaurant recommendations are pretty… basic.

One thing to keep in mind: Each itinerary is full of links to search for tours, some of which may or may not be useful. This is almost certainly how the creators of intend to make money: if you end up booking a ride, they’ll likely get a cut.

How about Istanbul, one of my favorite cities in the world? My wife and I spent a few days there last September, so to compare, I asked Roamaround to plan a three-day trip for me this coming September.

istanbul roaround itinerary

Well, okay. Sure, Hagia Sophia and the Blue Mosque are a must-see, but Hagia Sophia isn’t even a museum anymore – it’s a mosque. And go to Nusret Steakhouse for some “local Turkish cuisine”? You mean the over-the-top restaurants started by the man better known as “Salt Bae”?

OK, one last try for a city I know all too well: Hometown Minneapolis. Minnesotans know all too well that two days is enough for a visitor coming next January.

roamaround itinerary minneapolis

An afternoon stroll along the Mississippi Riverfront is truly amazing, but probably not in the dead of winter – it seems that’s recommendations may not take the weather or even the season into account. Oh, and dinner at Bachelor Farmer sounds good… in 2019. That restaurant closed in 2020.

Obviously, some itineraries are going to be much better than others.

What to look for when using

I am happy to turn to for ideas for my next trip. Not to plan the entire trip down to the minute, but for a starting point.

After testing Roamaround for a few hours, a handful of common issues and limitations have emerged:

  • We haven’t seen any recommendations for accommodation or places to stay, which is often one of the hardest parts of travel planning in a new city
  • It’s hard to know exactly how Roamaround (or, more importantly, ChatGPT) decides what and what not to include in these itineraries. But if you’re looking for a hole-in-the-wall meal or a hidden gem, it seems safe to say that these itineraries won’t uncover them – the most famous spots are often what we see pop. up.
  • can recommend a top-notch restaurant, but that doesn’t mean you can get in during your tour. The site clearly does not consider how difficult it is to secure reservations
  • Be aware of the weather when you stay, as Roamaround doesn’t seem to take that into account for their recommendations.

The bottom line

The future is here. Like it or not, AI and tools like this are going to dominate the conversation for the foreseeable future. And that includes the way we travel. is a promising new travel planning tool that can spit out pretty detailed itineraries and give you some ideas to get you started on putting your trip together. But for now, it’s best to look at these AI-generated itineraries as a starting point — and do some of your own research to back it up.

Try for an upcoming trip and let us know what you think!

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