FAMILY TRAVEL PLANNING
Creating travel itineraries for our family is one of my key “value adds”. AI is coming for me.
My expertise as the in-house travel planner was hard won. Between starting a business, and then a family, and generally being young and broke, we didn’t travel for decades.[1] We ALMOST travelled a lot, only to have some unforeseen work crises intervene. We collected travel books for places we never actually visited. These Fodors and Lonely Planets, with their glossy photos and tempting descriptions, mocked me from the bookshelf. I would gaze longingly at their top ten lists, fold out maps, and “must-do” recommendations. Their itineraries, optimized for the perfect 3/5/7-day getaway, were my ever-elusive Golden Rings. I resolved that if we ever went anywhere, we would put those guides to shame. We would Ace every destination.
Then, when we did eventually travel, it was with three little kids in tow. “Acing” a destination was not in the cards. Despite having a sheaf of “36 Hours In” at the ready, things went sidewise constantly. Things like: being denied our pre-paid family room at 1am; having no cash and discovering that your credit cards are frozen; being refused boarding onto a flight because the ticket doesn’t show your middle name; being refused boarding on a flight because your bag is bigger than a bread box; being refused boarding on a flight because they are double booked but Don’t Worry! there is another flight in three days; getting lost; getting heat stroke; getting food poisoning; getting pickpocketed; getting locked inside AND out of our rental. ALL of which happened on our first WTF vacations. Meanwhile, our three kids were looking to us as the travel experts when the only thing we were experts at was printing Bucket Lists off the Internet.
Since then, fueled by FOMO/YOLO goals, and informed by the many (so very many) lessons learned through trial and mostly error, I have nearly perfected the Capital-A Art of the WTF Travel Itinerary. These aspirational plans strive to thoroughly “tick the box” of every destination, while being as bulletproof as possible in the face of the other kind of WTF things that will inevitably arise.[2] They seek a delicate balance between leaving no experience un-experienced, while simultaneously avoiding the selfie stick forests of the Instagram crowd. To have every accommodation and meal be special, without breaking the bank. To have activities that hit the adventure/education/relaxation sweet spots of each family member, without pushing the others outside of their age/comfort/ability levels. This is no easy feat. Which is why all this talk about the “transformative power” AI on the travel industry makes me feel both threatened and defiant. After all, what can my limited experience add to the cumulative knowledge of every reference to travelling from all time? How can my paltry human research and analysis capability compete with a league of data crunching supercomputers?
And yet, in a contest of Parental vs Artificial Intelligence, I put my money on the Parent every time. Because even the most Intelligent AI cannot comprehend the weight of the death glares your screaming child will draw on a plane; or the panic of watching the subway door close with your child on the wrong side of it; or the acrobatics required to make a connecting flight while carrying/dragging/chasing small children and their associated strollers, stuffies, backpacks, and snackery. The AI has no skin in the game. The parent, on the other hand, has every fibre of their being in the game. And with WTF Travel the game is part Amazing Race, part Fear Factor, part Squid Game.
But let’s test this theory.
The first sign that ChatGPT is doesn’t really understand WTF travel is that every query returns a variation on the same upbeat, emoji laden, response:
“Planning a family vacation with young kids can be a blast — and a bit of a puzzle.😅”
“Kids on a plane can be both adorable and chaotic—kind of like flying with tiny, unpredictable CEOs.😅”
“Ah yes, the classic "car fight" scenario. Siblings and road trips—name a more chaotic combo.😅”
What Chat should say when asked about travelling with young children is: “You want to do WHAT??!!”, along with more appropriate emojis, like 😬🤮🙄💰🚽.
The next red flag is that Chat’s destination recommendations seem to use data sources that over index on theme park advertisements. When asked where we should go as a family with three small kids, Chat suggests: Disneyland, Disneyworld, Legoland (Denmark), Legoland (San Diego), and…Tokyo??? “Ah yes” … Disney Asia - and, also, “fun to eat panda shaped buns”. A 20-hour flight at a per person ticket cost of $2000 to an intensely populated place where we don’t speak the language? To go to a Disney theme park and eat panda buns? That sounds PERFECT!!
Tokyo Disney here we come!
First step: How will we survive the flight ChatGPT? Give me some tips! ChatGPT says bring “healthy” snacks. (Great! No parent, anywhere, ever, knows that one. Snack is required to go around the block.) ChatGPT says the kids can have “screen time – but not too much!”. (This, apparently, is the time to address the mental health crisis caused by on screen time?) ChatGPT says bring “activities like colouring books and playdoh”. ChatGPT says “bring a change of clothes”. ChatGPT says stay on normal eating and sleep schedules. ChatGPT says “don’t worry about the other passengers. They will be understanding.” These are all valid suggestions/pipe dreams. All that is missing is the critical In-Real-Life element.
Let’s play this out with our human brains: If you are luckt he activities you pack will occupy the kids for approximately the amount of time it takes to taxi to the runway. (And playdoh? Just, no.) The snacks will buy you another cumulative 7 minutes. Meanwhile, both these distractions will require about three hours of your attention to retrieve, assist with, pass back and forth across the aisle, and clean up. You will give up on your media consumption standards within the first hour, as the alternative is asking the “understanding” person sitting behind you to play an additional hour of peekaboo (which is cute exactly once) and to spare the significantly less understanding person in front of you from having their seat kicked incessantly. The change of clothes should be multiple changes of clothes, for both you and each child under your care, as well as a zip lock bag to hermetically seal whatever clothing needs to be replaced. And maybe a valium to help you recover psychologically from whatever barf/pee/Poo-Nami scenario necessitates use of this seemingly innocuous packing list item.
Fed, entertained, and changed, now it’s time to keep your children to their “normal sleep schedule”. This is no problem if by normal you mean the kids are jacked up with excitement and sugar overload from the airport Booster Juice that seemed like a good idea at the time. They will simultaneously be over tired and motion sick. There is also a 50/50 chance they will have an undiagnosed inner ear infection that will cause their heads to explode. Sleep won’t happen until the “prepare for landing” announcement and the seat belt sign switches on. You will be a human pillow for fully comatose children, made up entirely of pointy bits, with a combined dead weight of +/- a tonne. At this point you will have to beg forgiveness as you muscle off the plane first and run a five-mile sprint to catch your connecting flight. All while carrying not only your children, but all the assorted “make it fun for the kids” accessories that Chat recommended you drag to the other side of the world. This flight, if missed, will set off a Rube Goldberg chain reaction that will up-end every subsequent component of your vacation plan.
By the time you arrive at your destination, you will need a vacation…from your WTF vacation. You will then spend 7 days having, as Chat describes it, “a rewarding experience that will strengthen bonds, create lasting memories, and allow for shared discovery.” The bonds will be strengthened – but often through the ‘what doesn’t kill you makes you stronger’ method. YOU will remember every moment of it. The kids? Not so much. Which is okay because some large percentage (say…90?) of your discovery time will be spent in search of public washrooms, potable water, and “not weird” food. The other ten will be spent having a piggybacked child draped over your head, sound asleep and dripping sweat and drool down you face.
Not that you shouldn’t do it: you should. And use AI to help you plan - but remember, as with any shortcut/cheat, relying on AI guidance only takes you so far - maybe 5% (or 0.5?) of the way. The bulk WTF travel planning relies on good old fashioned parental intuition, motivation and insanity. You will have to read between the lines of Chat’s helpful lists and see beyond the façade of its contrived enthusiasm. And beware of deep fake “AI hallucinations”! Those “fun to eat” Panda buns look suspiciously like a 🐼 emoji.
Enjoy Tokyo Disney! I hear it’s “Classic” .
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[1] Outside of business travel, which is the opposite of fun travel and doesn’t at all count.
[2] As only a person raised in the “Gilligan’s Island” era can. A three-hour tour? What could go wrong? [Before you ask: Mary-Ann, obviously.]