How to Travel With a Group and Still Stay Friends

Not sure how to navigate — or avoid — the sticky situations that can crop up on trips with other people? Consider these expert tips a little extra “travel insurance.”

Words by Erin Zammett Ruddy
Illustrations by Eugenia Mello

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I just got back from a trip to Jamaica with my sisters, my aunts, and my mother, and I’m still kind of in shock at how well we got along because my family can be, well, family. But our flights were on time, the weather was perfect, the villa was more incredible in person than in the pictures, and the rum punch was plentiful, so we didn’t really have to remind ourselves to go with the flow — because the trip was flowing exactly as we’d hoped. Better, even.

I’ve also been on group trips that don’t quite go as expected, and those can get tense. Last year we rented a ski house with friends, and the temperatures rose into the high 60s. What was left of the snow melted, and each of us probably had an inner monologue that went something like “OM#*&@G I can’t believe we spent all this money on a ski house and we’re not even SKIING!!!!!” We managed to keep it together only because we were with our most laidback friends.

But you can’t always control who’s in the group — and even when the dynamic seems simpatico and things go according to plan, there are still those tricky aspects (picking rooms, figuring out meals, splitting costs) that can set anyone off. That’s why I tapped the pros for their secrets to group-travel success. Try these road-tested tips to keep your whole crew content.

Before You Go

Start a group chat. It’s easiest to have one designated text chain where you can firm up airport transfers, potential excursions, and the breakdown of the bedrooms — together. “The best way to go into a group trip is with everyone feeling like they’re in the loop,” says Chloe Florea, a vacation concierge who specializes in group getaways to Jamaica. It’s a great way to build excitement, too: In the weeks before our trip, we shared articles, Instagram screenshots, and the sunny forecast among our crew.

Be clear about costs. “It’s better to talk about how expenses will be shared before the awkward moments when the bills arrive,” says etiquette expert Diane Gottsman, author of Modern Etiquette for a Better Life. Decide how costs will be split — for the rental, for groceries, for meals out, and for transportation. Will someone put the deposit on a credit card and you’ll all Venmo?

Appoint a treasurer. Someone in the group will be good at figuring out tips and keeping track of who owes what to whom. My aunt Judy, who’s really smart and also a little type A, used Notes in her iPhone. At the end of the trip she had things like, “Ann paid $28 for taxi to Geejam, Cindy laid out $60 cash for Frenchman’s Cove entry, Melissa bought round of Red Stripes at the Blue Lagoon for $32.” (My husband swears by the app Settle Up for this, which he uses for guys’ trips.)

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Get ahead of hunger. If you’re renting a house where you’ll be cooking, it’s helpful to figure out in advance who’s doing what (the groceries, the grilling, the cleaning). Consider bringing some pre-made dinners that you can just heat up, especially for the first night, suggests Meredith Shanley, a personal chef in Huntington, New York. “If I’m going to be driving to an Airbnb, I always make a pot of chili, pulled pork, or meatballs ahead of time, freeze it, and bring it along in a cooler, and I pack lots of snacks,” she says.

While You’re There

Be strategic with room assignments. Rental listings include photos so you can scope out the digs, but you won’t definitively know where everyone should go until you get there. “You’ll set yourself up for a smoother trip if you take a tour of the house and make suggestions for who should bunk where, based on the personalities and needs of the guests,” says Florea. (If someone is known to get up to use the bathroom a lot, offer the room with the en-suite bath; if someone will be waking up early to run, the room off on its own is the best fit.) Figuring out who gets the master is probably the most significant decision, so “to avoid arguments and set expectations you may want to have this conversation ahead of time,” says Florea. I always let the person who found the house (i.e., did the heavy lifting) take the best room.

Disclose your sleeping habits. If you’re sharing a room with your friend and she doesn’t know you have to sleep with a nightlight, or that you sometimes sleepwalk or snore, speak up so there are no surprises (and your roommate has an opportunity to come prepared with, say, a white noise machine). “You should ask for what you need, too, whether it’s beforehand or during the stay,” says Allison Fleece, cofounder of WHOA, a boutique high adventure travel company for women. “If you’d like privacy while in a shared room, ask for 20 minutes to get ready, and offer to give her that in return. Communication is the key to a successful shared rooming situation.”

Set some house rules. “If you’re going to have kids with you, it may be a good idea to suggest a vacation family meeting where you can ask if there are any rules anyone wants to propose,” says Laura Markham, Ph.D., a clinical psychologist and author of Peaceful Parents, Happy Kids. (Sharing, manners, cleanup.) “When parents go on vacation, we’re looking for downtime, but kids need supervision, especially in the beginning. Giving them guidelines to follow will help things run smoothly.”

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Schedule solo time. Just because you’re in a group doesn’t mean you should never get to be alone. “I one hundred percent believe travelers should carve out their own time and space on vacation, especially when in a large group,” says Florea. “Wake up early and take a swim in the pool or a long walk, or draw a bath before going out to dinner. Taking an hour a day to unwind alone will help keep the energy in the group positive.” If you’re traveling with little kids, take turns watching each other’s children so you can do an activity (or even just shower) on your own.

If you didn’t plan it, don’t judge. Nobody likes a Monday morning quarterback. Every trip has bumps in the road, and those things don’t always need pointing out. “You don’t want to be the one toxic person who turns the whole trip into a complain-a-thon,” says Florea. “You can gripe when you get home.”

Wait a beat before snapping. If someone gets snippy, take a moment to breathe before saying something you might regret. “Step away from the situation and remind yourself that if someone does something to upset or annoy you, it’s probably not done maliciously or personally,” says Fleece. “By letting it go, you’ll make sure you don’t escalate the situation any further.”

Share your shots. So much of the joy of traveling comes from savoring the trip once you get home. (And by not obsessing over the taking and editing of photos when you should be enjoying the vacation moment.) Hours after we landed from our Jamaica trip, we all met up again for a glass of wine and to airdrop our pictures to each other. #latergram

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About the author: Erin Zammett Ruddy is a freelance writer living on Long Island. Her work has appeared in Glamour, HGTV, Marie Claire, Real Simple, Redbook, and Shape, and on the Yahoo! homepage. She is currently a contributing editor at PARENTS, where she writes about food, travel, home renovations, and, of course, kids. Follow her on Instagram.

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