Can ChatGPT Act as a Tour Guide? This AI Generated Tokyo Itinerary Shows it Can (with Some Caveats)

Andy Budd
7 min readJan 18

I’ve been visiting Japan for the past 10+ years, so friends often tap me up for recommendations. It happens so often that I created my own Tokyo guide, which I’m happy to share with anybody who asks. Recently a friend of mine asked for recommendations on LinkedIn, and another friend tagged me in the conversation. I was going to share my guide as normal, but for fun I thought I’d ask what ChatGPT thought instead.

I started with a super simple request — “Create a 7 day itinerary for Tokyo”, and I have to say I was impressed with the results…

The results were a touch generic; for instance by suggesting you check into your hotel rather than recommending a specific hotel, or that you have a farewell dinner at a local restaurant.

To make the itinerary a little more helpful I asked ChatGPT to recommend specific locations using the following prompt — “ Create a 7 day itinerary of Tokyo with specific restaurant, gallery, museum and cocktail bar recommendations.”

This itinerary was much better, and started pulling out specific places I love like Bar High Five, 21_21 Design Insight, and TeamLab Borderless, as well as some nice neighbourhoods like Harajuku and Omotosando.

It’s worth mentioning that Tsukiji Fish Market is best visited in the morning, so I wouldn’t put it after a visit to the Imperial Palace. It’s also worth noting that TeamLab Borderless closed down last year, so it’d be a long schlep from Omotosando to Odiaba only to find it no longer there. It seems like ChatGPT is picking historic recommendations, which to be fair, so is my list. However it’s definitely worth checking if these recommendations are still operating before heading off.

The results were still a little generic for my liking so I thought I’d try some specific qualifiers to see what happened — “Create a 7 day itinerary of Tokyo, for a young couple who like design, architecture, modern art, Japanese culture, hipster neighbourhoods, fine dining, street food, cocktail bars, dive bars, walking, parks and…

Andy Budd

Design Founder, speaker, start-up advisor & coach. @Seedcamp Venture Partner. Formerly @Clearleft @LDConf & @UXLondon . Trainee Pilot. Ex shark-wrangler.