The prompts to ask ChatGPT to plan your dream holiday

One limitation I discovered is that ChatGPT can’t look up actual flights to book. It responded to my question about looking up flights with: “As a language model, I do not have access to real-time pricing information or booking systems”. So I’d head to a website like my trusty Skyscanner if you’re airline-agnostic and just want to find the best deals.

Compiling an itinerary

Feeling ambitious, I knew I wanted to make it to a few different cities in Japan during my (hypothetical) dream trip there, but I still don’t know where should be on my hit list – or where would be realistic to travel to in the time I had available. Robot to the rescue!

This is what I asked:

I am visiting Japan for two weeks this September. I would like to visit three or four different areas while I am there. Which cities should I go to?

It came up with a hit list of four, listing Tokyo, Kyoto, Hiroshima & Osaka, listing for each some additional useful information, e.g:

“Kyoto: Kyoto is known for its traditional temples, shrines, and gardens, and is a great place to experience Japanese culture and history. The city is also surrounded by beautiful mountains and forests, making it a great destination for nature lovers. Popular attractions include Kinkaku-ji (the Golden Pavilion), Fushimi Inari Shrine, and Arashiyama Bamboo Grove.”

It also suggested some further places to visit, and why, e.g. “you might consider visiting include Hokkaido (known for its natural beauty and skiing)”.

Creating a planning checklist

Each journey of a thousand miles begins with a single step, so the Chinese proverb goes. But how about getting ChatGPT to list all those steps for you? That’s what I did with this next prompt, where I asked the AI to compile a checklist of all the things I’d need to coordinate ahead of my trip.

What should be on my checklist for planning a two-week trip to Japan in Autumn? I want to visit Kyoto, Tokyo, Osaka and Hiroshima

It came up with a 10-point list of things to consider, including sorting a Visa (if necessary), purchasing a Japan Rail Pass and learning some basic Japanese phrases. Also, packing. And on that note…

Writing a packing list

Finally, I got ChatGPT to pack for me. Not literally (although that would be the real dream scenario, tbh…) but in the sense of writing me a packing list of things to remember to put in my suitcase, tailored specifically to my destination and the time of year. I asked:

What should I pack for my trip to Japan this September?

I could also have gone ahead and asked it about specific cities or activities, adding, for instance:

Please include what I’ll need to go hiking in the Japanese Alps for a couple of days

However, for these purposes, I kept it general. I was presented with a 10-point list of useful things to consider, covering all the basics (toiletries, electronics, clothing including a light jacket and walking shoes), plus thoughtful additions like a foldable souvenir shopping back and respectful clothing for temple sites. Seriously impressed! Now, just to make this dream trip a reality…

Francesca Specter is a London-based writer and podcaster. You can follow her work by signing up to her newsletter, while she’s on Instagram at @ChezSpecter.