Unconventional Adventures
Ernest Shackleton was born tragically late.
By his birthday in 1874, the age of exploration had well and truly entered its twilight years. Nearly a milennium before Shackleton’s birthday, the Viking Leif Erikson had sailed to North America and established a settlement there. More recently, Admiral Zheng He had led the first Chinese fleets to Africa. Vasco da Gama had sailed around the Cape of Good Hope, finding and following the sea route to India. This is to say nothing of the many indigenous peoples, like those in the Polynesian islands, who were likely accomplishing similar feats even earlier.
Shackleton was arriving late to the ‘sail uncharted waters’ party, and so late in fact that most of the people at the party were dead by the time he showed up.
But while much of the world had been discovered and trodden by leagues of explorers, in the late 1800s there was still one part of the world left mostly untouched: Antarctica. And so it was, at least according to myth, that in 1900 Shackleton published an advertisement in the paper that you almost certainly have seen some version of.
It is unlikely that Shackleton ever published this ad. But he did eventually go to Antarctica, and not once but three times. And as the probably fictional ad suggests, he earned plenty of honor and recognition—plus a name among the halls of history’s most legendary explorers.
The Adventure is Dead
Shackleton was not the only great adventurer of the past. Before anything resembling modern transport existed, the default for anyone who wanted to go any great distance was to gear up for a complex, unpredictable, and possibly wonderful journey.
When disgruntled husband Martin Guerre abandoned his wife in 1548 and traveled to become a soldier in Spain, he probably did large stretches of his trip—like crossing the Pyrenees mountains—on foot. When the western European woman Egeria undertook a years-long journey to Constantinople, Jerusalem, and the summit of Mount Sinai, there was no high-speed rail network to take her there. When Christians went to Santiago de Compostela, or Muslims to Mecca, or Buddhists to Bodh Gaya, they often did it by walking for months on end.
It is not that people particularly wanted these journeys to be uncomfortable (no doubt a few 5th-century pilgrims would have gladly taken up the opportunity to fly Ryanair) but that they had no other choice. As it turns out, however, this constraint may have been a good thing.
You can imagine a Christian, mind set upon Santiago de Compostela, looking south towards the Picos de Europa in Asturias and wondering, Hell, is a cathedral really worth it anymore? Or a Muslim walking over the Nafud desert for the first time, watching the sun rise over those vast and wide alien sands. These must have been magical moments. In the past, experiences like these were inevitable if you were a traveler.
That is not the case today.
Here is something to try: ask ten of your coworkers where they traveled when they went to Europe and make a mental diagram of all the overlaps. Spain? Oh, just Barcelona. The Netherlands? Ah, only Amsterdam. Paris? Just the Louvre and the Notre Dame, oh, and those the stairs you saw in John Wick. This is being generous, even. If we are to compare the average tourist’s activities at a more abstract level—like how they traveled to their destination and what they did upon arriving—the responses would be similar regardless of locale. A flight, then a taxi, then a hotel. Some casual walking around. A few restaurants. A museum. Oh look, another restaurant!
And you even went clubbing?
We have two characters to blame for the same-ness of travel design in our era: Better Transport and Mass Media, Including The Internet (which we will forthwith shorten to Mass Media).
In 1914, pilot Tony Jannus took the world’s first-ever commercial passengers from St. Petersburg (the one in Florida) to Tampa (also the one in Florida). Commercial air was off to the
Better Transport, while an altogether wonderful person on balance, did a number on adventurous travel. If Martin Guerre had abandoned his wife in 2025, he could have simply hopped on a plane to Madrid and then grabbed a last-minute ticket on a train to northern Spain. A harrowing adventure, indeed.
Now it appears that Mass Media is over there in the corner thinking we have forgotten about him and that we are going to continue heaping insults on Better Transport. Let’s call him over, and let’s start before the internet. Arthur Frommer’s Europe on 5 Dollars a Day in 1958 was the first multi-million tourist guidebook bestseller in the United States, but many followed: the Let’s Go travel books from Harvard, Lonely Planet guides, Rick Steves books—perhaps you’ve seen some of these. The popularity of this writing snowballed down into travel magazines, first print and then digital, and finally into content on the platforms most people under 30 use to plan their trips: like TikTok, YouTube, and Instagram.
But wait. Shouldn’t the internet have made our trips more unique?
It could have. One theoretically nice thing about the internet is that it can be comprehensive and diverse. If you would like to plan a trip to Paris you no longer have to rely on a fixed number of suggestions in the guidebook you bought. You have infinite ideas if you search for them.
Unfortunately, this theoretically nice thing about the internet has been defeated by a sadly definite thing about the internet: it is great at creating hiveminds, at funneling 99% of attention to 1% of things. Now not only can the people who bought the guidebooks learn about That One Restaurant Only Locals (And You) Go To but you can learn about it, too, and so can anyone else with access to the internet, and probably you will each hear about it from a different influencer saying something different, though equally exaggerated, about it.
Perhaps the best way to visualize it is this: if you had arrived in Berlin two hundred years ago you would have had to chart your own course. If you arrive in Berlin today you will have, in the form of TikToks and Instagram and online guides, seen dozens of courses already charted for you. You will have formed an idea about what you are supposed to do there—perhaps even what the locals do. And if you are ever in doubt, all you need to do is grab your phone to access infinite, precise information as you explore the city.
The grand question, then, becomes: is there anything wrong with this?
You know, with the way we all travel today. Is there anything wrong with the fact that more than a third of the international tourism in Europe is concentrated in just 20 of its cities? Or that when we arrive, most of us do the same things: see the sights, walk around, eat at the same restaurants? Or that TikTok exists?
Here is the surprising part: there is not much wrong with that version of travel. Not all of us want an adventure when we go on vacation. Some of us want a restful flight to Europe, a luxury hotel, and a Michelin-star restaurant. Hell, I want that, most of the time. It’s nice to fly to a city, and leisurely walk around it, and eat and drink.
But whatever happened to adventure?
Long Live the Adventure
Until late July of 2019, only a few thousand people knew who Tom Davies was. At the time, they knew him for playing Geoguessr: a game in which you are placed in a random Google Street View location somewhere in the world and have to guess where you are. That was all he did. Geography nerds, myself included, were part of this niche audience. It was fun.
On July 19, though, Tom published an entirely different kind of video. Its title was a little crazy.
This came as a surprise to most of his audience, myself included. The guy I used to half-watch playing a geography game online had gone outside. And not only had he been outside but he had attempted to do something that, to the best of my knowledge, nobody in human history had ever tried before. Shackleton made it to Antarctica, sure. Zheng He made it to Africa. But did either of them cross the places they had explored in a perfectly straight line?
One can assume it is only rational that, in an age where anyone with an internet connection can pull up a high-resolution and real-time satellite image of almost any inch of the planet, true adventures must take a turn. No longer can you be the first to discover something (and who really cares about being the first, anyway). But you can challenge yourself to to experience part of our planet in a new way. And that is precisely what Tom Davies set out to do. It took him four separate tries to complete his straight-line mission—though complete it he did. It was, well and truly, an unconventional adventure.
It does not take much searching to realize that Tom is not the only person coming up with wild adventures. In late 2024, a man named Ed Pratt posted the first video in his series with the following title:
Ed begins his journey by walking in a field with a full-body wetsuit on (pictured above), starting at where the Thames is supposed to begin, and trudging on until he finds the first trickles of water. Those trickles become a creek, which becomes a river, at which point he picks up the kayak and makes his way all the way to the sea.
While Ed and Tom were subjecting themselves to borderline insane physical challenges, a group of three young American men were doing something rather different in a small town square in northeastern France. If you had also chosen to wake up at the crack of dawn and walk to the town square on that particular morning, you may have even been able to make the words out.
“We’re playing tag across Europe. We’re in Charleville, France, but that bell means it’s 6 A.M. and Ben’s the runner, so he’s gotta go go go!”
So begins the first video in the Tag Across Europe series from now-popular YouTube channel Jet Lag: The Game. The tone of their adventure is markedly different from Tom and Ed’s; they are not embarking on physically grueling solo adventures that pose great risk to their physical health. They are instead using the spectacular European train network to play a game of tag.
But tag, played as adults and across a continent, is more intense than you may assume. At one point one of the men thinks he’s going to pull off an early victory, only to be thrown off course by ferry times—and caught minutes later. During another moment in the season, the person running from the chasers hides in a photo booth in a train station to avoid detection (sort of like a Mission: Impossible sequence if Mission: Impossible was made by young men with one hundred dollars instead of one hundred million).
One common theme on the Jet Lag team’s podcast, The Layover, is that part of what makes their games so special is the places they get to visit. Places that, had they planned their trips out like the rest of us do, they never would have visited. Who books an obscure train into the French countryside on a whim? And who gets out at the most obscure station on that line and wanders the local village?
[This next part is from Carter’s POV. Hello!]
Last year I spent a few days hiking 100 miles in Spain’s Sierra Nevada mountains. When I returned to Madrid, wanting to make the most of my vacation, I decided to do something a little weird: to walk from the southernmost point of the city’s municipality to its northernmost point without using a map. This took all day, was equal parts interesting and boring, and was more difficult than I had thought it was going to be.
The route took me through parts of the city I would never have explored had I followed the paths that most tourists take. Early on in the walk, I popped in for early lunch at a (real) Chinese restaurant. I watched part of a rec soccer game in a neighborhood I don’t know the name of. I walked along the Rio Manzanares and watched how it twisted and turned and became more wild, more green, more beautiful the further up I went. Near the end of the adventure, I stumbled across what I thought to myself would be a great picnic spot.
I was hooked. In the months that followed I made it a goal to go out on as many unconventional adventures as I could. I defined these as strange, unplanned, physically exhausting, impromptu trips, with little to no research done online beforehand. Each was magical and memorable in its own way.
On one of these trips, in the rolling hills of the eastern Swiss countryside, I may have found the most beautiful bench in the whole wide world.
There is no one definitive template for the unconventional adventure, no rulebook to follow. While GeoWizard’s most viral series is his straight line mission across Wales, my personal favorite series of his is called How NOT to travel Europe, in which he and a friend make their way across Europe in some creative and unconventional ways. The Jet Lag team doesn’t just play tag—they play all kinds of games, like Hide and Seek and Capture the Flag. In my own life, I’ve chosen to focus my trips on finding off-the-beaten path villages and quiet corners in the outdoors. Your adventures will undoubtedly be different (and hopefully just as fulfilling) in their own right.
There’s one thing for certain, though: unconventional adventures are gaining in popularity.
In late 2024, the Jet Lag team released a version of Hide and Seek that you can play on public transport across your city or country. It sold out within minutes. Channels like GeoWizard and Ed Pratt amass millions of views in a matter of hours. On social media, the concept of traveling to gather “dad lore,” which is to say embarking on ridiculous and creative journeys, has become wildly popular among young men. Perhaps not everyone is wading in a cow-shit-filled Thames in a wetsuit, but it is clear that there is an increasing appetite for something different. Not for the same itinerary every travel guidebook has suggested for the past fifty years, but for fresh and unconventional ways to travel.
The adventure, it seems, is coming back.
And Long May the Adventure Reign
There was something wrong with people like Ernest Shackleton, wasn’t there? Who wants to mount a trip to Antarctica? That’s what you think, at least at first. But if you are at all inclined towards adventure, you see it. The glimmer that must have been in his eye. The adrenaline when he set sail. The highs and the lows and the glory of it all. There is something about an unconventional adventure that the routine experience of travel cannot quite deliver on.
Now it’s true that today there are not many places to discover. But there are more people than ever craving adventure. People who want to do something a little bit weird—a little insane. And those people are in luck, because we are currently living through an era of adventure. Not of setting sail to undiscovered lands, but of exploring the ones we already know in creative ways.
Like me, you may judge crossing a country in a straight line to be too grueling (and perhaps illegal) to warrant attempting on your own. And that is kind of the point. Your adventure should not look the exact same as everyone else’s. No, you may not be sailing in a ship to Antarctica. But you may be going on a crazy hike you didn’t plan in advance. Or navigating your city without a map. Or playing tag across Europe, or hide and seek across Japan. Or racing rickshaws across Sri Lanka. Or you may simply try exploring a new city without the help of guidebooks or the internet. Whatever you find yourself doing, it will not be conventional. It will not be the thing all of your friends and coworkers saw on TikTok and then did last summer. And most importantly it will, if you have the right constitution for it, be quite fun.
And then, after it’s all done? Sure. What the hell.
Go check into a nice hotel and enjoy that Michelin-star dinner.
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