9 Writers Share Their Most Adventurous Vacation Stories

Until Summer Fridays become legally mandatory in American office settings, we’ll have to rely on those precious vacation days we’ve been squirreling away since the new fiscal year started. Vacations, for many, mean an intentional refresh—the opportunity to clock horizontal hours and maybe hit the spa. Although it’s hard to argue the inherent luxury of a good pedicure, where’s the adventure in terry cloth robes?

Obviously everyone has a different definition for “adventure.” For some, that means jumping on the back of a stranger’s motorbike in search of illicit substances on an exotic coast. For others, it may mean just stepping outside their comfort zone—even something as vanilla-sounding as staying on the 13th floor of a mid-grade hotel could be pretty dang wild for some. Regardless of varying definitions, obviously writers will tell the best story about their mind-bending trips. We spoke to 9 about their most adventurous vacations. Buckle in—it gets bumpy.

In the mid-’90s, on a indiepop listserv, I fell hard and fast for the musician who’d made an album that got me through grad school. I’d posted something breathless and fawning, and out of the blue, he emailed me. We kept doing that. Then the packages arrived, with hand-labeled tapes of his own music, rare recordings of our (OUR!) favorite musicians, and bands that soon became essential to my being. Then a middle of the night phone call with a soft, sweet, shimmering Irish accent on the other end. I booked the ticket to London within days, was on my first-ever international flight within weeks, then there I was standing in Piccadilly Circus in front of the Statue of Eros with no plan and complete faith. A man—my future, my fate—threaded through the Friday afternoon throng toward me. He stopped in front of me. We smiled. There were no sparks. None. It was awkward. I recently saw that he blocked me on Twitter, even though I’d never reached out. I still listen to that album, though. Usually on a plane high above the Atlantic Ocean. — Kat Kinsman, Managing Editor at Extra Crispy

A few years ago, [my wife] Erin and I spent a couple weeks in India. We flew into Delhi, then went to Jaipur, then to Udaipur. There was a good bit of culture shock, and Delhi in particular was much too big to enjoy for us, but for the most part it was pretty doable. You get used to how different (and how hot!) everything is, the nonstop people in your face, taking the autorickshaws into busy city centers where it feels like death is imminent, etc. We spent something like 60 hours without a real bed toward the end of the trip (long train ride, then a car service, then plane to Paris, then plane home). And we did get totally scammed by some guys that resulted in a $350 multi-hour car ride between cities. (I think we got out of that one lucky considering it was just me and her and some dude who we didn't realize was a part of a scam until a couple days later when we talked to our travel agent.) Phew! I tend to like a slow-paced, drink-heavy kind of vacation, and this was not that! But I'm glad we did it. And the food was freaking awesome. — Austin L. Ray, Editor at Good Beer Hunting

When I was 18, some of my punk friends from San Pedro knew a guy who knew a guy, whose grandma owned what seemed to be a timeshare vacation property for retirees in Palm Springs. We somehow fit 12 or so teenagers into a strange-looking clay-colored house in a gated community of identical clay-colored homes on the perimeter of a golf course. The freezer was decked out with different types of coffee and frozen food even though the place felt like no one had lived there for months. I remember riding on a golf cart with my friend Danny and scaring old guys in white polo shirts. It wasn't the most adventurous vacation of my life but being 18 and stealing away for a weekend on plans we made-up on a Friday night felt magical. — Alina Nguyen, Managing Editor at The Hundreds

We were in Peru during a massive strike that essentially shut down transportation (train and automobile) throughout the entire Sacred Valley and cut off access to Machu Picchu for several days. We walked through the protest as they were rolling boulders and telephone poles into the streets, and we walked right alongside the railroad tracks as the protesters were ripping them up and lighting them on fire. Aguas Calientes, the town at the base of MP, is only accessible via foot or rail, so unless you were hiking the Inca Trail (which you have to have a permit to do, usually secured 6 months in advance), you were SOL. We were pretty determined to get to MP and ultimately it took us four days (and canceling the last half of our trip elsewhere in Peru) to do so.

I guess the Adventure part really happened when we ended up squeezing into a van with 15 other people, paying the driver $7 a person to drive us on a sort of terrifying and very steep unpaved road to a power plant called Hidroelectrica, which is as close as a car can get to Machu Picchu, and then hiking the remaining ~8 miles in the dark with our packs along the railroad tracks at night through the Andes. (We had been planning to start our hike in the afternoon, but another group of protesters had blocked a major bridge on the way there, so we were delayed several hours while we waited for them to let us pass. Our driver dropped us off about half an hour before sunset.) Clambering over train trestles above bodies of water in pitch black darkness with all of our luggage on our backs and nothing but a shotty flashlight to light the way was kind of nuts, but the stars were insane and the scenery (while we still had sunlight) was like something from Jurassic Park. — Gray Chapman, Contributing Writer at VICE and Racked

This wasn't really an “adventure” in the climbing-a-mountain, learning-a-new-language way, but I started traveling alone about three years ago, and the first trip I ever took all by myself was to Montreal. (See: not THAT adventurous.) After a breakup and a medical scare and some big professional news, I decided to take the train up from New York.

When I arrived I discovered that for some arcane bank-related reason neither my debit nor credit cards would be accepted in Canada, and I had no cash. I cried to my mom and thought the trip was a mistake, but I wound up reaching out to a few people I'd forgotten lived in the city, and met up with my AirBnB host, and everyone was so nice and willing to loan me what I needed to make it through the week even though I could have easily been scamming them all. (JK, I fear trouble way too much.) I wound up spending a lot of time hanging out with these new friends, and friends of their friends, and that in turn made me want to talk to bartenders and shop owners and miscellaneous Canadians. I loved being alone but not lonely, and that trip was so good that it compelled me to go on a big solo trip once every year—next was Berlin, and then last week I went to Paris. I liked realizing that I can solve my own problems, and that when I can't, there will be people who emerge to help me out. — Alanna Okun, Senior Editor at Racked

Shortly after college, myself and two friends decided to do a week-long roadtrip from Atlanta to New Orleans to Austin to Nashville and back to Atlanta. There was a lot of late-night driving, sleeping on people's floors, and gas station food. Our hotel in New Orleans had a power outage but I bought a really cool candle from a voodoo shop. Austin was hot as hell but we went to Hamilton Pool and splashed around and that was magical (plus breakfast tacos galore). Nashville was a fun town, we went to a bar that had cocktails with a piece of bacon sticking out of them. A very memorable trip! — Caroline Cox, Contributing Writer at NYLON and VICE

When I was 20, I studied abroad in London. For spring break, a couple of my friends and I decided to go to Santorini, Greece. Getting there was easy, but to get back we had to connect in Athens which shouldn’t have been as tricky as it was. We showed up to the Santorini airport hours early; so early, the entire airport was actually closed. By the time we finally got to Athens, it was around 6pm at night and we had to be at the Athens airport at 3 a.m. We sat our things down in the hostel and went outside to catch a cab to the Parthenon. Eventually, we got to the Parthenon. We knew it would be closed but we had the taxi driver drop us off anyway. We walk up, seeing the gates at the very bottom are closed. Then we realize we don’t know where we are. You want to know where the Parthenon is? Literally in the middle of nowhere. We start walking, realizing that my European phone isn’t working so we can’t call a cab. After we pass a couple questionable looking restaurants, we eventually find one called “God’s Restaurant.” The waiter looks like Peter Griffin, and is nice enough to call one of his friends who owns a cab. As we’re waiting, we walk over to the candy store next door. There’s an older man who welcomes us as we find our way to the gelato. Then, he starts singing to us “Welcome to Greece, welcome to Greece, welcome to Greece.” As we’re trying the gelato flavors he starts singing “very very nice, veryyyy nice, very, very nice.” It was wild. Eventually the cab comes, and as soon as he starts driving we freak out. People in Greece don’t follow rules on the road! They do what they want which is usually driving a million miles a minute! I remember being very scared up until we got back to our hostel, in which we spent about two hours in before leaving. I was very happy to get back to London. — Gabriela Herstik, Latinx Culture Writer at HelloGiggles

My brother goes to university in Spain, so I try to visit him at least once a year. Last November, I flew to Madrid for a much-needed post-election vacation. On my first day there, my brother got a call from the father of a good friend of ours. His son's birthday was coming up and he was looking for ideas of how he should celebrate. My brother, half-jokingly, suggested we fly out to Amsterdam—oh, his kids live in Amsterdam, by the way—to surprise him. Two days later, we got a call saying that we had tickets to Amsterdam. We scrambled to pack our bags and figure out our schedules—my brother had exams at the tail-end of this impromptu trip; I had a transAtlantic flight to catch and a job to return to the next day.

After we all had landed and gotten our bags, my brother received a call: we were to take a train into the city and await an Uber at a really nice Starbucks. [We boarded] the rain-slicked black Mercedes… [eventually] we pulled up to the Waldorf Astoria. I cannot emphasize enough how scruffy we looked in our hoodies and beat-up sneakers, asking for our suite. ... But as soon as we told them we were there for this birthday party, the staff softened and treated us like foreign dignitaries. "Right this way, sirs," they beckoned with that slight Dutch accent.

After we settled into our rooms, we hit the streets. We also bought the kid a bunch of vinyl for his birthday. Eventually, we hit a house party and stayed out much too late.

The next morning, we woke up and prepared for the actual birthday party in the Waldorf's lavish ballroom. Once we finished our ridiculously regal spread of seafood and steaks, etc. we decided to break out the vinyl. Mid-way through Dirty Sprite 2, a Waldorf employee politely stuck his head in the door and told the father (and host of this whole shindig), "Sir, I just want you to know that while we appreciate your patronage, you might want to turn the volume down. Otherwise, your fellow guests might file a noise complaint and we'll have to shut this party down." At this point, the father looked up and said, "No, they won't." He then went on to explain that he had bought out every room on that wing of the hotel to avoid said noise complaints. Wowed, the bellhop vanished. — Ben Roazen, Editor at HYPEBEAST

Anyone who truly knows me knows that I'm pretty much scared of anything that involves risks and rushes of adrenaline. While I'm a travel addict, I'm the farthest thing from a thrill-seeker, opting instead for serene and tranquil ways to explore culture, art and all that good stuff. That all changed when I went to Mexico's Yucatan Peninsula to ring in my 25th birthday with a group of about 20 travelers, most of whom were from Australia and New Zealand. These naturally adventurous and outdoorsy new friends were amused by my apprehension to let loose and pushed me to cross off a whole bunch of firsts as we traveled from Mexico City to Mérida to Cancun.

On that trip, I (almost) ate a grilled cricket—bringing myself to hold the charred acrylic nail sized-bug in my hand was an applaudable feat—and jumped my non-strong-swimmer self off a small cliff and into a fresh water cenote, or a sinkhole, with fish still swimming around. My initial dismount off a catamaran and into deep water for snorkeling was less than graceful (the captain spotted my silent struggle in the water and made me hold onto a life ring the whole time), but rewarding once I mastered my breathing and stuck my face beneath the water's surface. That is, until I cut my knee on the ladder while trying to get back on the boat. And finally, this non-license-having New Yorker drove a golf cart around Isla Mujeres with some friends alongside local traffic. This was all within the span of six days, six days that made me realize that while it's OK to be scared, pushing past the fear and living a little makes for way better anecdotes. — Stacy-Ann Ellis, Assistant Editor at Vibe Magazine​