How to Travel with Friends—Without Becoming Enemies

David Prior, the vacation guru and founder of the namesake travel club, has planned trips for Gwyneth Paltrow and normies alike. He can organize a group of strangers to have the time of their lives in India for Diwali, and he has an 80 percent return rate to prove it. But this year he has taken on the daunting task of planning his own trip.

For his upcoming 40th birthday, Prior, whose previous jobs included assistant to Alice Waters at Chez Panisse and stints as a writer and editor, is planning a trip for about 25 of his closest friends to Andalusia.

“There are people coming who are 25 and 80 and everything in between,” he says. “There will be food people, fashion people, people I went to school with,” including the illustrator Luke Edward Hall and the designer J.J. Martin. “It’s a mixed bag.”

The group trip has a fabulous and complicated history. Think of Yves Saint Laurent and Pierre Bergé in Marrakech having languid afternoons with John Paul Getty Jr. and Talitha Getty. Or, during the Jazz Age, Mark Cross heir Gerald Murphy and his wife Sara having Scott and Zelda Fitzgerald come to their villa on the French Riviera, along with Picasso, Rudolph Valentino, and Gertrude Stein. (Just how did they deal with the constant outbursts from Zelda, who, if legend is correct, stumbled around in a sleeping pill daze and did a lot of impromptu skinny-dipping?) More recently, Tilda Swinton and Haider Ackermann have been inducing bouts of FOMO with their group trips, which have included Ryan McGinley, Vik Muniz, and Waris Ahluwalia in the Maldives.

When done correctly—aperitivos for hours with a good view, dancing to Robyn in an unnamed Paris club in the Second Arrondissement, reminiscing about college in a cedar sauna—traveling with a group of friends is a seamless mix of fun and relaxation and exotic locales.

But like most things that look easy, the group trip has complex inner workings. It involves issues no one likes to talk about even on a good day, like money and whether you truly want to spend a week in Aspen with your friend’s new boyfriend who works in finance and plays pickleball. In other words, there is a fine art to traveling in groups—enough that it gives new meaning to the phrase shuttle diplomacy.

Diplomacy, yes. But the first rule of group travel is: This is not a democracy. “There is always one ringleader, typically the most type A character. They rally their group,” says Dayyan Armstrong, who founded Sailing Collective Travel Co., a New York–based company that will plan about 60 private yacht charters this year. Armstrong compares his meetings with trip organizers choosing destinations to therapy sessions. “You have to think about where you are in your life. Are you coming off a superstressful work time and want to be blissed out with tropical waters and nothing but mellow? Then you should go to French Polynesia, or Sardinia, or Antigua. Or are you looking for activity and action and want a lot of movement? Then you should consider the Gulf of Naples, the Croatian coast, or the British Virgin Islands.”

He adds, “It’s often fun to go with friends who aren’t your best friends.” Old friendships can mean a lot of history, but intimacy can breed conflict. After all, the whole point of going on vacation with friends is to avoid the kind of breakfast table drama that can blow up a family vacation. “There can be so much gossip and showing off with groups of friends,” says George Scott, who owns the Andalusian guesthouse Trasierra with his sister Gioconda and organizes group horseback rides (Christy Turlington, Poppy Delevingne, and Nacho Figueras’s wife Delfina Blaquier were one recent squad) with stays in old farmhouses.

Just how much everyone is willing to spend on a villa on Hydra or Majorca for a week is perhaps the thorniest issue. “One of the things that can make a group vacation weird or tense is money, because people have different capabilities and levels of comfort around it,” says Ezra Woods, who co-owns the L.A.-based showroom Pretend By Appointment. He goes on a lot of group trips, and they include everyone from actors to meditation teachers to interior designers, and he has found a few successful formulas: “Everyone splits accommodation equally, and then it’s nice if friends take turns hosting meals or activities.” (His inspiration for that was The Real Housewives.) “This way someone can host a dinner out for 10 people one night or pick up the tickets to an archaeological site or massages at the villa for everyone. Maybe another friend who has more resources could rent a boat for the day.”

But cut it off at one or two items on the itinerary a day. This isn’t a sightseeing bus tour or a class trip. “It’s grating when you feel obligated to participate in everything. If someone is over­scheduling, set expectations from the outset. Say, ‘I’m so excited, but I sense that I’m not going to be interested in doing every group activity,” says Christopher Golden, a yoga teacher in New York who plans retreats (Provence! St. Lucia! Oaxaca!) and goes on his fair share of trips with friends. “If I’m in Cape Cod with a crew, and everyone wants to go to the beach but I don’t, it’s nice to say no, and suddenly I have this huge house to myself. That’s when I really feel like I’m on vacation.”

Private space is important, whether that means having a room to yourself or not staying together at all. Traveling as a group, for adults, does not have to be a slumber party. Golden went to Paris with friends one spring, and part of what made it successful was that five people stayed at a mix of hotels and rented apartments. Some would make a pilgrimage to Dries Van Noten together, others to the Pompidou, but there was no pressure to do any of it. Every night they came together for long dinners that started with seafood towers and steak frites and ended with cheese courses and pavlovas, and they talked about their days. A room of one’s own can also avert disaster: everyone getting sick of one particular person, whether the reason is the person is high-strung or won’t stop talking or is a chronic complainer.

“Once I was on a retreat and everyone was sitting down for dinner, and I could tell there was one person they were all trying not to sit next to,” Golden says.

Which brings up another vital though often unspoken rule: It’s wise to have a shared level of hedonism. “Some people like to work out every day on vacation, and others don’t at all,” Woods says. Some travelers love nothing more than picking up a pack of cigarettes at the tabac for the full European experience. Some want to maintain their Paltrow–esque intermittent fasting regime no matter what. Some want to close out the local disco and use a rented house for the afterparty. Some would rather die than part with their phones for an hour (or, gasp, lose service altogether). There are no correct answers. To travel well together, you don’t need cohesion, but you do need to be able to coexist happily.

In the end the perfect group to vacation together is like the perfect blend of dinner party guests. It’s about chemistry, but also some wildcards and surprises. When Prior plans any trip, he thinks about it like a narrative with a beginning, middle, and end. His birthday will be no different: It starts with dinner at a long table at Trasierra, which he has rented out, then horseback rides and shopping for flamenco dresses (for women and men who want to play along) in the middle, and it culminates at Seville’s Féria on the last night.

Even though he has put a lot of thought into the guests, the setting, the itinerary, it still doesn’t mean Prior doesn’t have host anxiety. “It’s quite ironic, because I’ve never done a party for myself. I’ll have to get back to you about how it goes. It’s probably the one trip I’m more nervous about than anything else.”

Dear T&C

Traveling in a group is a minefield of etiquette questions. We’re here to help.

If I rent a villa or house with friends, who should get the best room?

Anyone who has ever watched The Real Housewives knows that one way of doing it is to manically run around assessing the bedrooms and then claw the eyes out of anyone who gets between you and the suite with the marble steam shower. Among civilized people, the following rules apply: First dibs goes to anyone paying for the entire trip (or a large portion thereof). If the cost is split equally, the person who found the house or did the most planning gets preference. The exception is if there aren’t enough rooms and two single people have to share; then they get to choose. Just remember that a small room is a better fate than spending a week with people who hate you.

If I invite people to go abroad to celebrate my birthday, am I expected to pay for their travel?

If you want 30 people to accompany you to Morocco for your 50th and have the means and inclination to foot the bill, go for it (and invite us). But in most cases it’s kosher to invite people to come to your destination event and ask them to pay their own way. There are two caveats:

1. Under no circumstances can you be offended if they decline.

2. You should host at least one central event—a dinner, a party, a snorkeling expedition on a fabulous yacht—for your guests during the trip. And, of course, no birthday presents.

My spouse and I are traveling with friends this summer, but for our sanity we need carve-out time away from the group. How can we do this without offending the others?

Lay the groundwork in advance. If you wake up one morning and awkwardly spring it on the group that you two are setting out alone, your friends may assume you’re irritated with them. Instead, during the planning stage, let them know that you’d like some private time to hike up a particular volcano on day three, and that you’ll meet them for dinner that evening.

I traveled with a group of friends and we all had a wonderful time, but now they want to make it an annual affair. Must these people now be my travel companions until I die?

This is tricky, especially if you do want to travel with this group ever again—just not as frequently as they’d like. The best strategy is to be so busy—with work, life, and, most saliently, more travel—that you can convincingly tell everyone that you can’t possibly fit another trip in the calendar before 2026, but you’d absolutely love to meet them in Positano then.

This story appears in the Summer 2023 issue of Town & Country. SUBSCRIBE NOW

You Might Also Like

• 12 Weekend Getaway Spas For Every Type of Occasion

• 13 Beauty Tools to Up Your At-Home Facial Game