ChatGPT is here to take a big chunk of stress out of your holiday planning. Take putting together the dream trip which you've already booked annual leave for, but have yet to sort out. There was a time, not long ago, that this process involved an impossible jigsaw puzzle of coordinating affordable flights, securing appropriate accommodation and navigating local transport. We'd scour online articles and travel books trying to identify the best hotspots and cities to cram into the time available; ask friends for their long and messily-formatted recommendations lists; bicker with our travel companions about the confusing logistics.
Further ago in history, we might have considered this an impossible task – roping in a professional travel agent to sort everything for us. Suffice to say, times have changed. In (literally) seconds, ChatGPT can give you straightforward answers to the questions you might have spent hours, days, puzzling over in the past. What's more, the AI-generated chatbot can whip up sleekly-formatted lists to spur you into action with your planning – think, packing lists and checklists of what to prepare.
Don't believe us? You're right: seeing is better than believing. Here are the prompts we suggest you feed to ChatGPT in order to get coordinating your dream trip. Before you test it out, we suggest you start by deciding how long this trip is going to be (for instance, this might correspond with the maximum annual leave you can book off work). From there on, ChatGPT has the answers…
Destination ideas
As it stands, I already know where I'm going on the dream trip lasting a fortnight: Japan! However, I was curious to find out what ChatGPT had to say. The first suggestion on its list was – surprise, surprise – Japan, presumably based on my past activity. However, it also suggested Australia, a tour of Europe and a Southeast Asia adventure. So that's future food for thought.
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Identifying the best time of year to go
Suffice to say, I know very little about when to visit Japan, beyond the vague recollection that people flock there around March/April for cherry blossom. As this time of year has already passed I'm going to need other options. I opt for the prompt:
It immediately breaks down the pros and cons of visiting in each season, according to different travel needs. For instance, winter is cold but ‘a great time to visit for winter sports like skiing and snowboarding’ on account of ‘snow-covered landscapes in places like Hokkaido and Nagano’. Instead, I opt for autumn – which offers ‘beautiful fall foliage’.
If weather is an important consideration for you (the temperatures weren't mentioned in ChatGPT's answers), I would add:
Next up, flights…
Finding the best value flights
One of the considerations I have about when i'm going to visit Japan is to do with flights, as flying to Asia can be pricey from London. So I asked the chatbot:
Thankfully, one of the two answers that came back was September to November, which is when I was planning to fly anyway (the other was January to March, the country's coldest months).
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:
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."
From finding cheap flights to creating a personalised financial plan, AI technology is here to help you.

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