If you read about AI and turn the page, thinking it’s not for you, or you’re too old to learn now, or technology and you never got along, or you use AI to do research or write papers, and stop there, you need to keep going. You must.
Because last week I used AI to plan a trip to Japan next year.
What I got back will not only change how Jean and I travel, but change how most everyone will travel. And travel itself, which is one of the world’s largest economic sectors, is a teensy thimbleful of what AI is already changing. Thorn.org uses AI to spot and reduce child trafficking, Seeing.ai narrates surroundings for the blind, StorySign translates text into sign language for deaf children, and Woebot offers mental health support. And on and on and ever-more-speedily on.
So here’s a beginner’s guide to making AI the best travel planner, agent, outfitter, guide, gourmet, sommelier, curator and concierge you’ve ever had – all for…well, for nothing, and all in 30 seconds, which is how long it took AI to create and spit out an hour-by-hour itinerary for us to spend 10 days in Japan.
First, it’s important to know that AI is only as good as your ‘prompts’, that is to say, what you ask it to do. I like to think of prompts as ‘briefs’ from my days when I briefed politicians. They had five minutes, and you had to figure out what they needed to know to be ready for their next meeting, often in five minutes. Most of the mental editing I did was figuring out what not to include in the briefing. The point is, be specific, precise, and because it’s AI and not a politician, feel free to include the kitchen sink. Because you can refine your search an infinite number of times. Forgot to mention how much you’re prepared to spend? Or that you’re a vegan? Or use a walker? Put that in a follow-up. One draft is rarely enough for writers or prompters.
You can start by logging on to the wildly popular ChatGPT site. Download it on to your phone or laptop. The basic model is free. But there are all kinds of sites you can use other than ChatGPT. I use Perplexity, because it provides the original sources for every fact, claim and reference that AI writes back.
Then you want to create the prompt. Jean and I have been to Japan before, and this time we want to see some specific places and do special things.
We want to spend a day in Hiroshima because we’ve been to Auschwitz in Poland and want to see the site of the world’s other war-torn horror. Also, my father served in the Pacific in World War II, a theatre of war I know little about.
We want to spend two days on Naoshima, the art island, because our friends who’ve been there say it’s out of this world. Plus two days in Kyoto which we missed on our first trip. We’re also avid kayakers and want to kayak the Tokyo River when we’re in that city for three days. And tour the giant new version of the Toyosu Fish Market.
Generally, we prefer ryokans to hotels, love insider cultural events, unflashy gourmet restaurants, and great guides.
I put all this into my prompt below, and in my second query, told Perplexity our budget is $500 Canadian per day for each of us.
“Create a 12-day itinerary for two older but very fit Canadians who are also sophisticated travelers to tour Japan in the late spring of 2026. We will spend one day in Hiroshima, plus two on Naoshima, plus two days in Kyoto and three days in Tokyo, with the remainder of the trip to be determined by Perplexity. We will stay in boutique ryokans, and love eating in excellent local restaurants off the beaten track. We also want to kayak on the Tokyo River and visit the Tokyo Fish market, with a personal guide. Please insert names of specific hotels and restaurants.”
Here's what Perplexity came back with in…30 seconds. As you can see, it’s at least 99% of everything we asked for, or could hope for.
So we have a choice: we can either book this trip ourselves, or ask our travel agent to do it, or get on sites that let you use AI to plan, book and pay for your trip, like Booking.com,Kayak, MindTrip, TripPlanner.Ai, Vacay Chatbot and many more.
Again, this was my first foray into using AI as more than a research tool.
I quickly tried other trips, both fanciful and real. An adult son wants to take his dementing father for a weekend in Montreal where they were both born. A week-long ski trip to Switzerland which is now in the same price range as a week-long ski trip to Whistler. A trip to Pamplona for the running of the bulls where you’ll run with the bulls too.
And a limitless variety of other trips, driven by your newly freed imagination.
Yes, I’m fresh in the embrace not only of a new tool, but a toolbox that’s infinitely long and deep. No salmon restaurant will ever escape my patronage again. No river will elude the prospect of my paddling down it.
But the first thing I’m going to do is the first thing I urge you to do:
Take a course. Scott Galloway and Section looks tempting, as do the online AI courses from Canadian universities. And from IBM. And the Toronto Public Library offers free courses on how to stay ahead with artificial intelligence
In short, you won’t have to look far to dip your future into this brave new world.
So be brave and…just do it.
Meanwhile…
1. The Story of a Heart. Dr. Rachel Clark is a British doctor whose book just won The Women’s Prize for Non-Fiction. It’s the tale of one girl dying and giving her heart to a boy the same age who flourishes today because of that transplant. Read it and weep.
2. They’ve got rhythm. First, can we call this ballroom dancing? Next, Spanish dancers.Plus, a new way to dance to Don’t Stop Me Now. Finally, fist dancing.
3. You’ve got questions; we’ve got…Is it okay to earn rental income from an ICE holding facility? Are psychedelics the new key to better sex? Do you love wildlife? Do you picture wildlife? Do we have a contest for you. And is Sumo Wrestling the sport for you?You don’t have to be gigantic and Japanese. And how can you improve your kitchen-life?
4. How spies predicted Israel’s Tehran attack. They simply clocked the huge uptick in pizza deliveries to the Pentagon the night of June 12.
Speaking of spy-mistresses, Britain’s MI6 has appointed the first female chief in its 116-year history. Blaise Metreweli, 47, is the new “C”...and like her female counterparts in MI5, Dame Stella Rimington, Baroness Eliza Manningham-Buller and Anne Keast-Butler, she has a name James Bond would die for.
5. One solution to the housing crisis. Turn empty offices into rental apartments. A Toronto developer, Toboggan Flats, is doing that right now.
6. How to…pass as middle class. Play the world’s smallest violin. Walk away from a plane crash. Create your own time zone. Design a metaphor from the bottom up.
7. Taking on…The Depraved, which Scott Galloway does superbly…British School Kids,which Mark Carney does deftly…Harm Reduction which Andrew Potter does humanely…and Willpower which has fallen prey to Ozempic.
8. Make-goods on bad things. The British Library restored Oscar Wilde’s library cardafter it was cancelled 130 years ago for gross indecency. Plus Ronan Farrow on Elon Musk’s real addiction. Finally, even America has high-speed trains Canadians can only drool over, and they’re nothing compared to Europe’s.
9. The landscape’s changing for….sponsoring balls. And for celebrity auctions, likeDavid Lynch’s archive. And Princess Diana’s effects. And for The Eiffel Tower…and even for fake AI-generated Snow Leopards.
10. People can flourish, as can families and nations. Or they can wither. The firstGlobal Flourishing Study was released last month. It polled 200,000 people from 22 countries and found young people are really struggling; religious communities play a big role in how well people flourish almost everywhere; and rich countries have fallen behind on meaning, character and relationships.
Followed your advice and got the Paris trip in September all figured out. Thanks Bob!