What 25 Years Of Traveling Solo Has Taught Me About Vacation Hookups

As a longtime solo traveler and travel writer, I’ve had my share of sexual encounters while globetrotting (occupational downside: serious relationships are difficult to maintain). In a recent article about the phenomenon of travel friend flings, I noted that there’s something about “being away from the daily grind that enables travelers to let loose with their sexuality, and likewise attracts the attention of others.” The change in locale can also result in increased self-esteem and a spirit of carpe diem. By sharing some of my past experiences (the good, the bad, the ugly), I hope to maximize your chances for a vacation hookup that won’t leave you wanting to chew your arm off the next morning as a means of escape. You’re welcome.

The first rule of travel flings is don’t try to have one. Trying too hard means you’re either guaranteed to strike out, or you’ll end up exchanging bodily fluids with someone who, while seemingly captivating in the smoky, late-night haze of the village pub or seaside taverna, resembles Quasimodo by light of day. (This is also a good time to note that hooking up doesn’t have to actually involve sex.) It’s been my experience that the less prepared I am to hook-up, the more likely it is to happen. On Christmas Day, 1999, I was camping on a Southeast Asian beach, when I came down with the flu, combined with bronchitis. I somehow managed to find the last vacant room on the island — a cell-like bungalow that mercifully had a Western toilet. I spent the next week riding out a high fever accompanied by a truly disgusting cough. Fortunately, a large group of Aussie friends were occupying the adjacent bungalows. In between drinking copious amounts of beer, they took care of me, bringing me water, Gatorade, and medicine. Even in my sweaty, phlegmy, semi-delirious state, I noted that one of them — a devastatingly handsome, sweet-natured guy I’ll call H — seemed to be dropping by more frequently than the others. When my fever finally broke on New Year’s Eve, I joined the Aussies in celebrating the millennium. I was haggard, weak, and stone cold sober due to the antibiotics I was on. H spent much of the evening by my side, and I was shocked when he kissed me in the final moments of the 20th century. What followed was the kind of night that can only happen when you’re 8,000 miles away from home on a tropical island, with zero expectations. We spent hours talking at an abandoned rooftop bar, then wandered down to the deserted beach, where we lay under a palm tree and talked some more. As dawn broke, we went back my bungalow, whereupon he threw me against the wall and kissed me. It was game on, and while we never technically had sex, we spent the next two days together.

When H invited me to cruise up the coast with him on a friend’s sailboat, I said yes. I was smitten, and he was talking visits to Australia. But things got weird after we pulled anchor, and by the time we reached our destination, he was acting paranoid, asking where I planned to stay that night and suggesting it not be in X village. It was obvious that something was up, and a month later my suspicions were confirmed by one of his friends, with whom I’d struck up an email correspondence. H had a girlfriend, and the reason he’d sailed up the coast to begin with was to meet the girlfriend he’d forgotten to tell me he had. I was humiliated, not to mention angry that I’d been made an unwitting accomplice to H’s infidelity. Regarding infidelity, let the buyer beware when it comes to travel flings. If you’re in a relationship, whatever your arrangement, don’t be an a-hole: use a condom. I don’t condone cheating because S.O.’s usually find out (“What happens on tour stays on tour” is bullshit in this era of social media), hearts and trust are broken, and diseases are spread. Potentially risking the life of someone you care about (or that of a stranger) is just not cool. If you’re single, be aware that your new friend may not be — no matter what they tell you. Since you have no way of knowing, in the moment, what their situation really is, protect your feelings and your health. I once had a fling with a guy, only to find out later that he was married. I don’t like being the other woman, even if the primary woman is cool with her husband screwing around. This brings me back to condoms. Condoms don’t work if you don’t use them, and if they’re applicable to your sex life, pack them, because you never want to rely on a rusting vending machine in skanky bars or off-brands from developing nations. Of course, condoms aren’t fail-safe, nor do they protect against every STI, but they’re better than nothing. On the related topic of safety, keep your wits about you when traveling, whether or not romance is on the menu. If you’re lucky enough to get lucky, don’t trust that your new partner will be a gentleman during or after the act, no matter how charming or heartfelt he is.

My first travel hookup occurred at 19, when I was a recent non-virgin traveling with my parents in Australia. I met a lanky, pouty-lipped Melburnian and let myself be seduced by his accent, swoon-worthy utterances, and amazing kissing technique. This is how I found myself naked in a hostel bunk bed in the middle of nowhere, sans condom (or dignity). After kicking his dorm mates out, all vestiges of romance left the building. “Let’s get this over with,” he said, and immediately proceeded to jackhammer me into oblivion. Then — despite his promise to walk me back to my hotel, which was two miles away down an unlit, treacherous coastal road — he rolled over and fell asleep. I wound up doing the walk of shame in pitch darkness, and had to break into a run at one point because a lecherous freak making vaguely threatening sexual comments began following me in his car. I swore off sex for the next year (true story). My best travel fling happened under the worst possible circumstances. It was September 11, 2001, and my next-to-last night in Portugal. I had just enough money left for a taxi to the Lisbon airport (my connecting flight back to the U.S. was via London). A shopkeeper with limited English attempted to explain the tragedy that was unfolding in New York, and at his urging, I called my parents from a pay phone. Dazed, I returned to my hostel, where I spent the next three hours slumped in front of the communal TV in a state of shock. Finally, a Dutch guy (who, I couldn’t help noticing, was extremely attractive), asked me, “Are you American?” When I said yes, he came and sat beside me, took my hand, and said, “Is there anything I can do to help you? Do you have enough money?” I’m not a spiritual person, but this guy, P, was my savior for the next 36 hours (while I waited for flights to resume). He did more than loan me money — he and his friends were determined to distract me. They took me to dinner that night, and despite my protests (it felt wrong to even attempt to have fun with so much pain and suffering at home), they dragged me to a club, got me blind drunk, and we danced the night away. Inevitably, however, I broke down, and P took me to a quiet corner and wrapped his arms around me until I stopped sobbing. It was exactly what I needed at that moment.

The sun was up when we got back to the hostel, where P and I proceeded to make out on the roof. After regrouping, that night we went out to see a fado (a Portuguese musical genre) show, and although I was emotionally wrecked, exhausted, and bedraggled from two weeks of backpacking, there was no ignoring the chemistry between us. Since we both had dorm mates at the hostel, our only option for privacy was the communal room, which was dominated by a pool table. I’m not an exhibitionist, but at the time, oral sex (reciprocative) on an expanse of green seemed like a great idea. And it was — until I saw a beam of light moving toward us from the hallway. In our hormone-addled state, P and I hadn’t considered that there might be closed-circuit cameras. The security guard was about to bust us. P and I leapt off of the table, scrambling for our clothes. He didn't move fast enough, so while he huddled, naked, behind a door, I pretended to search for a lost contact lens under the glare of a flashlight. Because the guard didn’t speak English and P (and his clothes) weren’t in evidence, he reluctantly let me be. P and I ended up becoming friends and stayed in contact for years; to this day, I’m grateful to him for the kindness he showed me (and I’m not referring to the oral). Sometimes, travel flings can remind you that humanity still exists, even as the world crumbles around you. While hook-ups in inappropriate places are part of the fun, vigilance is key. In college, I thought it would be fun to make out with a guy while lying on the bar in an after hours, open-air restaurant. It was a blast — until the local Federales caught us. One handcuffed hour in a janky cop car later (during which time I jabbered the only Spanish I knew: “I’m very sorry,” and “I have money”), we were relieved of all of our cash and dumped on a dirt road, forced to hoof it back to our respective lodgings. My roommates had no idea where I was, so if anything truly bad had happened, I really would have been screwed. The takeaway: try not to break any laws, and always carry (well-hidden) cash. And that, in essence, is the secret to a great travel hookup: Be ready for anything, and if you happen to know a few key words of the local language, so much the better.