Illustration by Salini Perera
Sometimes, we keep it simple and go to a cottage. Other years, we journey farther, to the Bahamas, Palm Springs, Mexico and Spain, where we walked the Camino de Santiago to celebrate our 50th birthdays. While our lives have taken us in different directions, my girlfriends and I stay close because each year, we reunite to catch up and laugh until our sides hurt.
Our trips have been planned and executed with so little friction and fuss over the past 40 years that we never considered a friend trip could be an absolute bust. We’ve since realized how lucky we are to have a group that travels so easily together.
Friend travel can be fraught: personalities can clash and resentments build. In worst cases, tempers erupt and a dream trip with friends becomes a nightmare.
One of the most common mistakes Calgary travel consultant Andrew De Angelis sees people make is naively assuming everyone will get along fine – just like they do when they see each other socially at home.
“That easygoing dynamic can suddenly change when you’re travelling with a person 24 hours a day,” warns De Angelis of Civilized Adventures.
Long before flights are booked, Julia Hayhurst, founder of Toronto’s Hayven Travel, says it’s important to talk about what each person expects from the vacation. Everyone needs to be comfortable with the budget, the destination, the itinerary, even the personalities in the group.
Aly Tsourounis, owner of Toronto-based public-relations agency ART PR, says it is smart to book a holiday with a planned activity in mind, such as tennis. (Courtesy of Ruth + Bud)Supplied
“If one or two people are unhappy with any of those things, hurt feelings and resentments can build, eventually ruining the trip, and possibly, even the friendships,” says Hayhurst. Before you go, everyone needs to talk about basics, such as: How active do you want to be? Do you want to travel with a guide or not? Do you want to share rooms, or each have your own?
Aly Tsourounis, owner of Toronto-based public-relations agency ART PR, has travelled many times with girlfriends, and over the years, has learned how to make each successive trip run smoother than the last. For instance, she met a small group of women through her daughter’s school, who hit it off instantly, and decided to go away for a four-day weekend. They chose a tennis trip in the Bahamas.
Given that they were all still getting to know each other, it was smart to book a holiday with a planned activity, she says. Their mistake was not choosing one individual to be the “voice” of the group. “Everyone was piping in, with ideas and suggestions, but no one wanted to overstep, so we were almost too polite,” says Tsourounis. “A couple of girls didn’t drink and wanted to go to bed early. Others wanted to stay up late. That wasn’t communicated beforehand.
“The next time we went away, we had a frank and honest conversation beforehand about what we wanted to do. That trip was so successful, the next year, we took our husbands.”
She is now in the throes of planning a 40th-birthday trip with eight girlfriends, whom she has known since high school. One of the women – a former management consultant turned stay-at-home mom – has taken the reins. Tsourounis said her friend did a “brilliant” thing, and sent everyone an anonymous SurveyMonkey with questions such as: What budget are you comfortable with? What are some of the places you would like to go (and do not want to go)? What time of year is most convenient?
“From the outset, we agreed: majority rules,” says Tsourounis. “Establishing ground rules is key.”
One great way to get everyone pumped about a trip is to start a dedicated group chat for sharing information and posting pictures of places they’d like to visit or things that inspire them, says Annie Pattillo, co-founder of Antigua-based travel adviser firm Ruth + Bud. Then it’s imperative to put one or two people in charge of the overall process.
Annie Pattillo, co-founder of Antigua-based travel adviser firm Ruth + Bud, says the bottom line 'is you have to pick the right friends for the right trip.' (Courtesy of Ruth + Bud)Supplied
“If you’re not working with a travel designer, make sure you split up who does what in terms of booking hotels, excursions, restaurants or flights,” says Pattillo. “If you are working with a travel specialist, you still need someone to communicate the needs of the group. In other words, I need to know if the majority want to fly and flop on a beach or if they want to wake up and go golfing or hit an 8 a.m. yoga class.”
She also can’t stress the importance of choosing your travel companions wisely. Travelling with your college roommate or best friend from work might seem like a great idea, but you must consider if your likes and dislikes are in sync.
“The bottom line,” she says, “is you have to pick the right friends for the right trip.”
Group travel tips
Julia Hayhurst has a few more suggestions to make your next friend trip the best one yet.
- Don’t feel you need to spend every second together. It’s okay to go your separate ways and reunite for meals.
- Honour everyone’s need for downtime. Some people feel recharged by sleeping in, taking a nap or getting a massage. Others may recharge with an early-morning workout or a round of golf.
- If you’re travelling with friends who like to post on social media, have a quick chat about your comfort level. If you don’t feel like being featured in photos, make that clear ahead of time.
- Figure out the best way to split costs. Some pool their money in a “kitty” at the start of each trip, others use apps, such as Splittr and Splitwise.
- Go with the flow! Travelling with friends may require compromise, but it’s 100 per cent worth it.