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Our Most Embarrassing Travel Stories

At Jetsetter, embarrassing travel moments come with the job. And considering how often we travel, you can bet we have our share of them. Here are our most cringeworthy, from lighting a hotel on fire to hiring a male escort (no, really.)

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That time we talked dirty in Italian

"One summer I was traveling around Italy, and after a few weeks there, I felt confident enough to try my hand at ordering lunch in Italian. It seemed simple: Voglio un calzone, per favore. Easy, right? Not so much. As the word calzone exited my mouth, my tongue stumbled, blending the L sound into an elongated Z, which came across as cazzone. To my horror, the 80-year-old Italian man sitting next to me burst out laughing as his modest wife (apparently Catholic) crossed her chest. Had I butchered the phrase that badly? I was too embarrassed to ask. The man, trying to catch his breath between gasps and guffaws, finally said in broken English, "You... you say... you like a.. big.." and gestured to his lap. All I wanted was an innocent sandwich, and instead — thanks to one misspoken letter — I asked for a slang word so crude, even Urban Dictionary would be ashamed." —Anonymous

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That time we hired a male escort

"For spring break, a group of my college friends and I drove down to Miami for a cheap week of fun. Our first night there, we went to a club on Ocean Drive, and after some much-needed liquid courage, I finally worked up the confidence to talk to a guy I'd been eyeing all night. He was tall and handsome—a local, I presumed, from his tanned skin and wind-tousled hair. After grabbing a drink and joining him on the dance floor, we really started to hit it off. Save for the memory of entering the number from his business card into my phone, the rest of the night was a drunken blur. The next morning, my friends and I hit the beach and I decided to call up crush. He arrived looking fit, smoldering, and categorically out of my league, and the afternoon was spent swimming, drinking and soaking up the sun. At the end of the day, as we were packing up, he turned to me and said, “Did you want to settle up now or after?” “Settle up for what?” I asked, confused. He looked at me and shot up an eyebrow, “...the day? You did look at my business card, right?” Apparently, I had missed the fine print (MALE ESCORT), which resulted in a $500 "service" fee. The best part? My broke ass couldn’t pay for it… so I had to call my parents"—Anonymous

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The time we set a hotel on fire

"My sister met her fiancé in Thailand and in a nod to their time there, I purchased floating lanterns to light and release at her bachelorette party with good wishes for their marriage. It would have been a great idea, but her bachelorette was in Palm Springs…during a drought. After a drink or six by the pool at the hotel, we went to the empty lot next door, wrote down our wishes, lit the lantern and released it into the air. It rose beautifully against the pink sunset…until a gust of wind picked up and slammed the lantern into an electrical wire over the hotel where it burst into flames, spraying sparks and fire onto the roof. RUNNNNNN, someone screamed. Everyone scattered while a security guard with a walkie talkie called who we imagined to be the police. As lifelong rule-followers, we huddled behind bushes and in alleyways near the hotel, convinced of our impending incarceration. Since I was the instigator of this ill-fated plan, I eventually decided to take the fall and confess. I strode from behind the bush about to approach the security guard, who was still screaming into the walkie talkie beneath the fireball. As I rounded the corner, it flamed up again…then went out completely, a small puff of smoke the only remaining evidence. I kept right on walking and from that moment on pledged my allegiance to Smoky the Bear. After all, only you can prevent wildfires."—Anonymous

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That time we got stabbed by sea urchins

"I stupidly decided to swim near a bunch of rocks on the Costa Smerelda and was knocked in every direction by some heavy surf. I dragged myself out of the water and onto shore, with dozens of black spikes embedded in my hands and feet. We drove to a nearby town, my hands and feet throbbing, and stopped in the pharmacy staffed by precious elderly women—as they are in all small Italian towns. I couldn’t find the word for “sea urchin” in my Italian-English dictionary, so I drew them a picture. The chorus of ladies—kerchiefs on their heads and everything—grabbed my hands and shouted various curses and/or prayers to the Holy Family, passing my palms off to the next and the next, each examining them in turn. Then they sold me some ointment that smelled like gasoline and sent me on my way."—Anonymous

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That time we got stranded at sea...well, kind of

"My then boyfriend, now husband, and I were vacationing in Mallorca and he insisted on taking me sailing. It was really windy and I resisted at first, but he convinced me the weather was no match for his skills. We took out a catamaran and within 10 minutes the perfect storm appeared — I swear the sky looked like the end of the world! The boat capsized and no matter how hard we tried, we couldn't flip it back around—we were literally both hanging on the sail with all our weight in pouring rain, but nothing helped (and my husband is 6.4"!). After a couple of hours, we figured we were going to die out there—we couldn't see land anywhere—and we sat on the top of the boat, talking about our lives together as the sky got darker and darker. Another three hours past (at this point it was pitch black) when we suddenly spotted a little fishing boat and started screaming, "Ayudya, Ayuda (help, help)." The boat threw us a rope and brought us to shore—the funniest part was we were just about a mile from land! Two things I learned that day: 1) Never trust a man who claims he's an amazing sailor. 2) If you want to get a man to marry you, have a near death experience with him."—Clara Sedlak, Executive Editor

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That time we got thrown off a horse

"I worked briefly at a horse farm in New York, where I was hired to exercise backup horses during shows. During one big show upstate, I had to take a particularly jumpy pony out for a ride. We started off and everything was going just fine—that is, until he spotted an obstacle that would require him to jump over a large pool of water. Too spooked to clear it, he stopped right before making the jump, which sent me flying over his head and into the water. Soaking wet and covered in sand and mud, I had to first chase after him and then walk from the ring dripping wet, as top coaches from around the world looked on." —Anonymous

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That time we got lost in the desert

"My then boyfriend, now husband, and I were on a 4-corners, southwestern, US of A road trip. We arrived at our destination by dusk and after setting up camp, watched the sky set against the dunes of White Sands National Monument. The next day we rose early to explore. We spent the whole day out there—even after our water supply ran out and the sun slipped dangerously low in the sky. When we finally decided to head back to camp, we set off in the wrong direction and got lost. White Sands National Monument is surrounded by a mountain range—there are no landmarks and everything looks the same. Panicked, we started towards the tallest dunes we could find, figuring that we would have a better vantage point from high up. After what seemed like eternity, we spotted a hiker far away and began yelling and running in his general direction. (Bear in mind, that at this point, I'm so parched that I can barely make sound.) We lost him, but somehow ended up on the main road and were able to hitch a back to camp from a bunch of Europeans. Looking back, I guess I'm thankful for that experience, because once you've tackled something like that as a couple, everything else is by comparison smooth-sailing."—Anonymous

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That time we sprained our ankle because of a puppy

"Over the summer I was lucky enough to go on a whirlwind two-week trip to Malaysia. Dead in the middle of my trip was a hiking jaunt to Gunung Mulu National Park, a super remote expanse of caves, karst formations and equatorial rainforest. On my first day at the park, I successfully hiked Deer Cave, the world’s largest cave open to the public, and in 100 degree heat, no less. So come day two, I was pretty confident in my hiking. After taking a four-person motorboat down the Melinau River, we stopped at a small handicraft village. Once out of the boat, I immediately spotted a tiny, fluffy black puppy just off the sidewalk. Determined to pet him, I blindly stepped off the sidewalk and directly into a foot-sized hole, audibly cracking my ankle. The pain hit me immediately, and with my group ahead of me already perusing crafts, I crumpled to the ground, ugly sobbing and watched my ankle swell to crazy proportions. Soon, locals began to move towards me and while I couldn’t understand what they were saying, a kind man tried to comfort me by bringing me the exact puppy I had sprained my ankle for. In the presence of perfect strangers, I continued to cry and hug the puppy until my group noticed I was missing and circled back to find me."—Chelsea Stuart, Assistant Editor


That time flirting didn't quite work out

"I flew to Mumbai a few years ago to attend a college friend’s wedding. During the mehendi at her house, the groom’s college roommate and I immediately hit it off, but I took things slow since I knew I’d see him later on at the cocktail party being held at the Trident Hotel. That night, our group of friends were dancing on the elevated dance floor when he excused himself to get us more drinks. I saw the moment to make my move. Once he reached the bar, he turned around and we made eye contact—then suddenly, I took a full-on stumble off the dance floor. Smooth." —Anita Ng, Photo Intern


That time an unexpected visitor visited our

"It was the end of a two-week trip through New Zealand and my travel group was staying at a hostel in Christchurch. All was well until we were woken up in the middle of the night by a man who'd run into our room from the hallway wearing a bandana over his face. He pulled my friend off his bed like a robber and then ran out of the room laughing. It was a prank (he was also staying in the hostel), but we were ready to go home afterwards." —Elizabeth Mullen, CRM Marketing Specialist


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