Nine tips to keep friendships intact while vacationing with pals

While there's a lot of potential for things to go awry on friendcations, there are ways to keep everyone smiling.


By SHIVANI VORA | Special To The Washington Post | Published: September 6, 2019

Ellen Sinopoli's vacation with friends to Cabo San Lucas two years ago had all the makings of the perfect getaway. The interior designer from Upper Saddle River, New Jersey, was traveling with her husband, Joe, their two teenage children and two other families with whom they were close friends. "We had vacationed with one of the couples before and had a blast and were excited to include the third because we all got along so well," she says. "What could possibly go wrong?"

But it turned out that the third couple had a travel style that clashed with how the first two couples like to vacation. For example, the Sinopolis and their tried-and-true vacation friends were keen to spend their days jet skiing and snorkeling, while the third couple preferred to relax. Come dinner, the two compatible couples sought out local restaurants, some of which were high-end, and liked to eat around 8 p.m. The third couple, on the other hand, wanted to find budget-friendly buffet joints and dine no later than 6.

In the end, there was a blowup, and the fallout was so bad that the first two couples never spoke to the third after their return.

In theory, a vacation with close friends — known as a friendcation — sounds like a great idea. But while you might enjoy someone's company over dinner, on the tennis court or while cheering on children from the soccer sidelines, a getaway with the same person or people could be a recipe for disaster. Interests, the goal of the trip, budgets and tolerance for togetherness all factor into the outcome.

Friendcations are on the rise in the experience of Krishnan Menon, founder and CEO of the Los Angeles-based marketing company Phenomenon, and several other travel specialists contacted for this story. Menon believes the trips' popularity is driven, in part, by social media. Groups post images and stories of trips with friends, and others "then want to recreate those moments with their own friend groups or use them as a mechanism for reconnection with distant friends," he says.

But while there's a lot of potential for things to go awry on friendcations, that doesn't mean that they can't be done. Here are nine tips on how to have a friendcation that's memorable for all the right reasons.

• Talk honestly before even agreeing to vacation together. This is key so that you can get a better understanding of each other's travel style and decide whether it makes sense to take the trip in the first place, says Roberta Long-Kelleher, a travel consultant with Protravel International in New York, who has planned dozens of trips for groups of friends.

Do you all want a vacation where you visit historical sites, for example, or are you more interested in shopping and dining? Are you seeking an adventure with nonstop activities or a do-nothing-all-day beach getaway? Also, while discussing money can be awkward, you need to have an honest talk about budget. How much are you hoping to spend on the trip, and does it align with what your friend has in mind? Do you have any flexibility with that number?

"It sounds basic, but many people don't have this crucial discussion and may not be on the same page going into the trip," Long-Kelleher says.

• Communicate while planning the trip. Jack Ezon, founder of the luxury travel advisory firm Embark, says that it's best to avoid a group text with endless messages or an email thread that clogs up your inbox. Instead, try apps such as Prava or Travefy, which help you organize your itinerary, store details such as everyone's flight information and also have messaging functions.

Or consider working with a travel adviser who can lead the communication and anticipate any problems. "Group trips take a lot of coordinating, including arranging flights so people arrive at similar times. I've had people come from all over the country," Long-Kelleher says.

• Designate a leader. "Pick one decision-maker who outlines the plans and presents them to the group beforehand with an open mind to compromising to balance everyone's wishes," says Ezon, who has planned more than 100 friend vacations. "Too many leaders will create havoc and confusion wherever you go and tension amongst yourselves."

• Work out sleeping arrangements beforehand. If you're renting a house together, Ezon and Long-Kelleher say that discussing room allocations — who gets the master bedroom, are the parents' bedrooms close to their kids' bedrooms — before the trip is crucial. "A lot of times, people all want the same room type, and deciding who stays where can cause friction," Long-Kelleher says. Ezon suggests prorating the cost of the home by bedroom size.

• Don't overplan (with one exception). Ezon says that he advises his clients to have an itinerary in mind but be open to change. Long-Kelleher agrees that a jam-packed agenda can put too much pressure on a group.

The one area where it's important to plan is dining, to plan meals and pick restaurants that can accommodate everyone's dietary restrictions. Long-Kelleher suggests having group members look at menus to make sure everyone is satisfied. Make reservations well in advance, especially during peak season. "If you want to have a special meal at a restaurant, you don't want to be disappointed about not getting a table," she says.

• Take time for yourself. Ezon says that space from one another is a must. "The key to a successful group trip is to have private time, whether it's to shop, go to the spa, hit the gym or explore a museum on your own," he says. "Leaving or joining the group should be fluid, with no judgments."

• Let an app sweat the money stuff. It's easy to lose track of who owes what money and to whom on a friendcation. Rather than struggling to do the math at the end of your trip, consider downloading an app such as Splittr or Splitwise to help you keep track of money throughout your vacation.

• Be careful with social media. You may be excited to show off your good times on Instagram or Facebook, but your friends may prefer privacy. "It's one thing to post pictures of yourself, but it's another to post them of your friends without asking their permission," says Michael Holtz, the founder of the high-end travel company SmartFlyer. "There's a lot of sensitivity around social media, and you don't want to damage a friendship because of it."

• Be flexible. Long-Kelleher and Ezon say that any harmonious trip with friends means some compromise. Remember, you're there for the company, not to have it your way all the time.

Giving in on some points may even add to your appreciation of the trip. A few years ago, Marjory Hawkins, a consultant from Austin, visited Paris with two close college friends. Hawkins had already been to the city more than a dozen times, and one of the friends had also visited before. But it was the third friend's first Paris visit, and she was eager to see the major tourist attractions. "I didn't necessarily want to line up to see the Mona Lisa again, but she was so excited that I went with the flow," says Hawkins. "In the end, I had a great time, and it was wonderful to see a city I love so much from the perspective of my dear friend."