The double-edged sword of AI-powered travel


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The double-edged sword of AI-powered travel

According to Time Out magazine, the “small and quirky” suburb of Otsuka is a hidden Tokyo gem with “some seriously authentic food and drink on offer amidst its “tiny winding pedestrian streets and World War II-era architecture.” (DLKR / Pexels)


AI is reshaping industries everywhere— including travel.

Wait, travel? As in, in-person trips to places? Um, surely that’s one sector that’s more or less immune from AI, right?

Wrong. But don’t take it from me. Take it from McKinsey.


The world’s oldest and largest management consultancy says that AI is about to usher in a new “golden age” of travel — on par with the advent of commercial jets in the 1950s, or the online travel booking revolution of the 1990s.

See, AI is about to let all sorts of travel sector firms augment their workers’ capabilities, and unlock greater operational capacities. (The examples they give include airlines using AI to help train their crew schedulers, or a hotel app that lets guests know if all the treadmills are taken before they head down to the gym, or order “room service“ from a ghost kitchen if the hotel’s restaurant is closed.)

But wait, there’s more. When it comes to marketing these new services, AI promises to let firms hyper segment their audiences, so they can deliver messages that are ultra tailor made to your and my interests.


Reading McKinsey’s report, I was reminded of a recent piece by the thoughtful strategist Alexi Gunner. Last August, he wrote about the rise of aesthetic tourism, aka “the vibe tourist,” that is, travelers inspired to visit places by what they see on social media.

Enjoying aperitifs at the trattorias of Rome and dining at the pizzerias of Sicily is not just about the cuisine, or service, but must now also feel like a scene from a movie, an opportunity to unlock a meaningful chapter in your personal narrative.

In TikTok terminology, the ideal holiday is a week of building core memories, where the vibe tourist feels like the main character.

Alexi Gunner, “Idle Gaze” 054

The downside of traveling like this is, of course, the disconnect or disappointment that vibe tourists feel when their café of choice or intended viewpoint does not live up to the curated, soundtracked expectations they saw on their Reels. (Alexi points out other structural flaws to vibe tourism, like the fact that perpetually “overcrowded plazas and packed alleyways” literally ensure that the vibe tourist “is never the main character.”)


Waiting for a treadmill to free up is totally boring. And it takes a uniquely sunny disposition to find the positives in having to scrounge for a late night meal in an unfamiliar town.

The vision McKinsey lays out —of hyper segmented marketing campaigns, efficient crew scheduling, or predictive insights about hotel amenities— is a glimpse of a slick (frictionless) future, where travelers (vibe tourist, and traveling salesperson alike) have everything they need in the palm of their hand, with minimal effort or inconvenience.


Is there a hidden value to some of the frictions we are all forced encounter while traveling? Like, how exploring to find that late-night meal could lead you to a hole in the wall that you'd never find on Eater, or how there is, in fact, joy to be found in successfully overcoming a challenge?

And, if so, will the AI x travel innovations that McKinsey predicts somehow rob travelers of the spontaneity that often defines the spirit of “going somewhere?”

Don’t get me wrong: I like operational efficiency, personalized offerings, and greater convenience.

But I also can’t help but wonder what travel would look like if AI were to augment/manufacture some of travel’s more baroque friction points.

Stay with me.


When cars first rolled into the world, many expected “horseless carriages” to introduce an era of unparalleled mobility, freedom, and convenience.

They did, but over decades, additional impacts associated with the adoption of automobiles revealed themselves. Suburban expansion. The replacement of large swaths of city centers with highway infrastructure. Pollution.

Cars did and do offer individual freedom of movement. And that freedom also contributed to a shift in transportation patterns, nowhere more so than in the US, where people remain less reliant on communal transportation than the rest of the world.

My point: The most interesting part about the rise of the automobile is not the cars themselves, but the ways we humans have organized our cities and living spaces around them.

This nuance provides a fascinating framework for analysis.


As with cars, the question is not AI good or AI bad? It’s how we humans are going to decide to wield it.

The travel sector’s most thoughtful senior executives are likely thinking about the intended human benefits of automation, hyper segmentation, and increased convenience as much as they are thinking of the operational benefits.

In our view, some of the most innovative firms in the sector may end up deliberately using AI to manufacture some glorious moments of friction, happenstance, and serendipity.

The history of technology is a testament to human adaptability but also to our occasional oversight in understanding the larger societal implications.

What I’m getting at is this: it's often not the tech itself but the human response to it that really defines its impact.

We’re at this crossroads with AI right now.

Countless firms —including my own— have been harnessing generative AI chatbots and imagemakers all year for efficiency and convenience. But how many firms are using AI to enhance human experiences in deep and meaningful ways?


In travel, where experiences are at the heart of the service, this presents an exciting opportunity for forward looking brands.

Look for them to put AI tools to work streamlining our journeys, while simultaneously introducing moments of serendipity. For instance:

  • A travel site that —based on your search and booking history— leaves one evening of your stay open, and suggests a surprise event to fill it.

  • An airline that offers a “can’t resist” deal to a random city you’ve never flown to, in a region you’ve never searched for —complete with guides to hidden gems in that locale.

  • Or a map that deliberately takes you the long way, literally leading you to the unexpected and the new.

I like these thoughts. However, I can’t help but think that the intentionally “wrong” use of AI, in order to get to an unexpectedly serendipitous conclusion is a really big idea, one that’s actually much larger than the travel sector.

I’m calling this the “intentional misuse theory” of AI, and I look forward to exploring it with you in future issues.

Stay tuned.


“The promise of travel in the age of AI” (McKinsey) »»

“The plight of the vibe tourist” (Alexi Gunner) »»

This FamilyMart in Shibuya has a hidden bar serving Japanese whisky and cocktails »»

Written by Jon Kallus. Thank you for reading. This newsletter recently took a 3 week hiatus thanks to an exceptionally busy period and, more importantly, so I could spend more time with my family. It’s good to be back, recharged, and more excited than ever about the friction between fate and future. Any feedback? Just hit reply!

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