Picture this: You’re sitting on the rocky shoreline of Paros, a Grecian island. Shouts from local fishermen are drowned out by the sound of the Mediterranean Sea’s salty waves crashing below your feet. You’re holding hands with a man you care deeply about, talking about the future—your shared future—and what you both might want out of it.
The catch: you met barely 48 hours ago.
It might sound like a scene from a reality dating show, but it’s an experience I and many other gay travellers have had. We travel to drink, to dance, to show off that flashy new Speedo–and along the way we meet someone who we feel an undeniable spark with, and that chemistry is reciprocated. Enter the vacation boyfriend.
The characteristics of a vacation boyfriend are simple. Be it a local or a fellow traveller, here is someone who you did not know prior to your voyage but quickly fell into a routine parroting that of a relationship: making plans, holding hands, sharing meals. I found myself with one such vacation boyfriend on a recent trip to Greece.
Why Greece? As someone who works in television, I found myself with a rare few weeks off while my show was on hiatus. My friends, however, did not share that same luxury–and few wanted to leave Canada during its most beautiful summer months. I knew I wanted to spend my break travelling, but I’m not well-versed in solo travel and prefer the dynamics of larger trip groups. So, I looked online for queer group trip options.
After some amateur googling (“gay, Europe, summer 2024, group travel”), I found Contiki’s Greek Island Hopping trip. While Contiki is not exclusively a queer travel company, they run some of their group trips just for LGBTQ2S+ travellers. The timing of Contiki’s Greek trip worked for me, and I couldn’t shake the idealized image of being drunk on a boat belting “Mamma Mia” as I bounced between beautiful islands. I signed up for the two-week excursion.
So, too, did Jake–a clever, kind-hearted, six-foot-five Aussie with a mischievous smile that would melt your heart. I was smitten on the very first night. Fortunately the feeling was mutual. At the welcome dinner in Athens–a delicious multi-course meal featuring traditional Greek staples like the eggplant-heavy moussaka and cabbage-wrapped dolmas–I made a half-toast, half-“this is what we should all do tonight” speech that, he says, is when he first set his eyes on me.
There’s a version of this story that involves a multi-day courtship that culminates in confessing feelings for each other on the black sand beaches of Santorini, but that is not our story. I don’t know if it was the aphrodisiac Greek seafood, but Jake and I paired up faster than you could say, “Sir, unfortunately Lindsay Lohan closed her Mykonos beach club.” Despite how many times we changed hotels, buses or ferries as we moved between islands, Jake and I always seemed to find each other. So much so that there are photos of us napping on each other on shuttles between walking tours, or kissing next to the white-painted windmills of Mykonos.
But now that I’ve reshored to Canada, and with Jake quite literally on the opposite side of the world in Australia, I’m ready to peel back both my sunburnt skin and the true benefits and pitfalls of having a vacation boyfriend.
Advantage: You are never the odd man out
Unless you’re the type of traveller who plants their ass on a beach or patio for the duration of the trip (more power to you), chances are you’re going to find activities to do. In Greece, these activities included two-seater paragliding in Mykonos, two-seater jet skiing in Ios and a sunset table for two along the edge of a Santorini cliffside. Noticing a pattern? When you travel as a group, there’s always a chance you’ll be the awkward third or fifth wheel, and as a solo adventurer half the fun of these moments is sharing them with someone. With Jake, I had a guaranteed partner in crime—and someone to split the bill with.
Disadvantage: Your fellow travellers might get annoyed
With a vacation boyfriend, you might be having the time of your life reenacting the scene from Titanic on every boat ride with your new paramour, but the people you’re travelling with didn’t sign up to witness love blossom. There’s a reason the bridal party doesn’t join the honeymoon. Add to that the excessive PDAing (of which Jake and I had plenty of—it’s Greece!), and others might greet you with, at best, eye-rolls and, at worst, a crowbar to pry you apart. While more emotionally independent travellers may not care what others think, as a double Gemini I unfortunately am hypertuned to the whims of others and as such paid greater attention to when and how Jake and I interacted in group settings.
Advantage: The sex is good and there when you need it
Though this may be as true at home as it is abroad, hooking up can be tedious work. Whether scrolling on apps or scanning the bars for suitors, it takes time to find people you want to get naked with. Potentially even more so abroad, when you don’t know where to look and so rarely can host. You don’t want to waste valuable vacation time on logistics. With the vacation boyfriend you don’t have to, since the fireworks felt upon meeting translate to the bedroom. On our trip, Jake would sneak away with me for some action while the rest of the travellers were sipping overpriced cocktails at a Mykonos beach club.
Disadvantage: You might not get to be as much of a slut as you wanted
Having sexual adventures can be one of the things that makes travel fun. Visiting a new country opens up an entirely new pool of hotties (or in my case, a pool bar full of them) to smash faces with. No matter what arrangement or understanding you have with your vacation boyfriend, you can’t help but consider his feelings if you’re out together and find yourself tempted to ditch him to taste some locally sourced meat. Nor can you stop yourself from feeling even the tiniest bit hurt if he does the same. I couldn’t help but pout when, one time, Jake excluded me from a hook-up back at the hotel–despite the fact that the very next night I was lip-locked with a Spanish tourist right in front of him. Even if the relationship itself is short-lived, it’s hard not to let real feelings get involved.
Advantage: Souvenirs become heartfelt keepsakes
Admit it, it’s a little cheesy to buy yourself souvenirs. The Greeks even have a custom against it; tokens depicting the Evil Eye only ward off misfortune if given to someone else. With a vacation boyfriend, even the most trivial of gift shop purchases are imbued with more than just memories of the destination. As I write this, I’m looking at the appropriately nude bust purchased when Jake and I went shopping together in the quieter island of Paros. Picture Michelangelo’s David with just the best bits. Suddenly the little bust holds deeper meaning: a connection to someone who so quickly and deeply cared for you, and a reminder of what is possible in your future.
Disadvantage: The “will they/won’t they” dance at the end of the trip
You knew this was coming, as does every vacation boyfriend. When the vacation ends, the airlines ask for check-in details, and then it’s time to say goodbye. Though it might feel naive, there’s an impulse to keep the relationship going. It feels good to love and be loved, despite how artificially pumped it is with two-for-one mojitos. I believe a good vacation boyfriend leaves, at the very least, a window cracked open to the potential of future visits and communication. At least that’s what Jake and I decided, committing to regular video-chatting from home, even as we lugged our overstuffed suitcases to our final ferry back to Athens for departure. (So far, that’s a commitment we’ve fulfilled.)
But we’re open-eyed about the challenges of a Canada-Australia connection. A vacation relationship is like Athens’ Acropolis. It’s okay if it stands preserved in history, a testament to people gone but not forgotten.
