Organizing a group trip with a gaggle of gays can be like producing a low-budget reality show. You’ve got the princess, the high roller, the penny-pincher, the slut, the “easy” one (who actually isn’t) and the one who wants everyone up at 7 a.m., so the group can visit every single possible attraction and all the pastry shops he saw on Instagram.
Like producing any reality show worth watching, a lot has to happen before the cameras start rolling. Especially if you want a second season—that is, for everyone to still be on speaking terms when going your separate ways at the luggage carousel. A gay group trip takes radical honesty, logistics and a sense of humour. Whether you’re heading to a circuit festival or a quiet villa in Portugal, here are six essential strategies to ensure that there’s no radical unfriending upon your return home.
1. Money talks
Money is the most common fracture point in any group dynamic, particularly when the definitions of “splurge” and “budget” vary among friends. Ignoring the disparity between your CEO buddy and freelance artist ex is a recipe for stress and resentment. To avoid the menu anxiety that happens when someone orders the wagyu while another is wondering about splitting a side salad, you must establish a financial baseline before a single flight is booked. Start with an anonymous survey where everyone submits their comfortable “daily spend” and their hard limit. Allow those who aren’t on board the opportunity to drop out gracefully.
The goal is to find a middle ground where the lower-budget friends don’t feel pressured into debt, and the higher-budget friends don’t feel as if they’re not #livingmybestlife. Use technology to keep the peace. Apps like Splitwise or Settle Up can prevent contributions from being overlooked and take the pressure off someone having to be the bad guy quizzing everybody about who ordered room service or collecting cash post-trip. Nominate one person as the banker to pay for group expenses like Ubers, groceries or villa fees on a single card to maximize points, then settle up at the end of each day. By removing the constant “Who owes what?” math from the dinner table, the group can focus on the experience rather than the invoice. If the group wants a high-end splurge night, make it optional, so individuals can opt-out and do cheap local eats without feeling like they’ve failed the group.
2. The libido spectrum & hookup etiquette
Sexual expectations vary wildly, especially if it’s a mixed trip of couples and singles. One friend may be looking for a romantic moment, while another views the trip as a 72-hour hedonistic marathon. These differing libidos can create tension, especially regarding guests in shared spaces. Before you leave, have a candid discussion about house rules. If you’re staying in a villa or sharing hotel rooms, what is the policy on bringing guys back? Figure one out before an orgy breaks out in a room where someone wants to read.
If the trip is a boys-only bonding experience, some may find it disruptive if a stranger is making coffee in the kitchen the next morning. On the other hand, if it’s a party trip, the accommodation should have enough “zones” or soundproofing, so that those who want an early night aren’t kept awake by the, uh, socializing of others. If space is limited, build some private time into the schedule. The friend who hates museums (and who is sleeping on the couch) will appreciate knowing that the Airbnb will be empty one afternoon.
Couples often default to their own bubble, which can leave single friends feeling like they’re third-wheeling on their own vacation. Encourage integrated activities where couples split up or focus on the group dynamic to ensure no one feels like an outsider in their own circle of friends.
3. Build free time into the schedule
Don’t pretend that everybody wants exactly the same trip. The fastest way to make someone miserable is to force them into a “mandatory fun” schedule that starts before they are prepared to have their first coffee. In any group of gay men, social batteries charge and drain at different rates. Make sure there is lots of “choose your own adventure” time built into the schedule, daily if possible. Group activities should focus on activities or excursions where it’s more likely that your group will want to arrive and leave as a group, like a sunset boat cruise, a dinner or a guided tour. Activities like museum visits—where each person’s interest or pace may vary—are better left as optional or to subgroups. Gym rats need time to find a local boot camp, the shoppers to hit the boutiques and introverts to hide away for a nap at the hotel. By normalizing opting out, you eliminate the guilt that often plagues group trips. If someone doesn’t want to go to the beach because they’re feeling body-conscious or just tired, a simple “No worries, see you at dinner!” goes a long way. This autonomy prevents group-think fatigue. Nobody wants passive-aggressive comments on day three of a trip.
It’s also a good idea to come to a general agreement about what to do when travellers do things at different speeds. When someone lags, is it okay for the group to continue or should they wait? Should everyone leave the club together or can each guy stagger his departure? If someone isn’t coming home because they’ve made a new friend and are spending the rest of the night with them, should they message the whole group or just make sure one person knows what they’re up to? (Of course, at least one person should be informed what they’re up to.)
4. Let subject matter experts take the lead
Decision paralysis is the silent killer of many a gay vacation. You’ve got six guys standing on a street corner in a foreign city, staring at their phones, asking, “I don’t know, what do you want to do?” for 20 minutes. To avoid this, treat the trip like a production and delegate roles based on each friend’s strengths. The logistics queen handles the flights, airport transfers and check-in details. The vibe curator is in charge of the playlist and scouting the best bars or clubs. The foodie handles restaurant reservations (and actually calls ahead to ensure the table can fit a group of eight). When everyone has a territory, they feel invested in a trip’s success. Too often, a group dad makes all the decisions. He ends up feeling stressed and unappreciated while others feel unrepresented in the decision making. The group needs to agree that an expert has made a choice, the rest of the group follows through without grumbling. This strategy has the added side effect of helping build self-esteem among the experts and building trust among the group.
5. Managing strong personalities
Gay peer groups can be remarkable in the breadth of types of people they include. It’s only a single step of separation from nerdish culture vulture to fashion-conscious party boys. These types might blend better in your hometown—where everyone can just go home when they tire of each other—than in seven straight days in a shared space. One or more travellers might emerge as the complainer or the diva or the person-who-thinks-they’re-funny-but-they’re-just-being-a-bitch. Everyone on a trip should come prepared to dial it down a notch. And the person closest to each princess/curmudgeon/free spirit should be prepared to pull them aside and remind them that in small groups, harmony is as important as self-expression.
6. Host a meeting to set expectations
A week before the trip, hold a mandatory trip meeting—preferably over drinks. This is less about the itinerary and more about ensuring everyone on the same page and getting everyone excited about having fun together. Is everybody dressing up for the Saturday night dinner? Wearing leather to the main event? Use this time to voice any last-minute anxieties: “I’m actually feeling a bit nervous about the budget,” or “I’m planning on taking it easy on the drinking this trip.” Remember that the primary goal is to celebrate friendship. Conflicts and grievances need to be put on hold. When the inevitable travel mishap occurs—a lost suitcase, a rained-out pool day or a closed nightclub—remind yourselves that the destination is secondary to the time spent together.