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Going on vacation with friends? Read this first.

Wendy Diep thought all of her friends were on the same page when they booked a trip to Disney World and Universal Studios in Orlando a few years ago: Roller coasters were most definitely on the itinerary. She was unfortunately mistaken. “One girl didn’t ride …



Going on vacation with friends? Read this first.
Going on vacation with friends? Read this first.
Wendy Diep thought all of her friends were on the same page when they booked a trip to Disney World and Universal Studios in Orlando a few years ago: Roller coasters were most definitely on the itinerary. She was unfortunately mistaken. “One girl didn’t ride roller coasters at all, and everybody wanted to ride roller coasters,” says Diep, the co-founder and CEO of group travel planning app Let’s Jetty. “We had to assign someone to hang out with her because she didn’t want to hang out alone.” Mismatched expectations are just one of the many ways a vacation with a group of friends can go sideways. When you’re traveling, you’re faced with dozens of decisions you don’t always have to make in your daily lives, says Auston Matta, the owner, founder, and CEO of the travel advice and LGBTQ group trip planning website Two Bad Tourists. A group of friends can often have conflicting ideas of where to eat, what to see, how much to spend, and how to get around. Add in the stress of being in a new place and disagreements are bound to arise. But you don’t have to let the possibility of conflict deter you from jet-setting with your pals. Most of the planning and discussion should take place before your bags are ever packed. Here’s what experts say will make your friend getaway as pain-free as possible. First, figure out the kind of trip you’ll take Group travel usually comes together one of two ways, Matta says: one friend decides on a destination and loops others in, or a few people commit to traveling together and they choose a locale collectively. Regardless of how the idea originates, everyone should be on the same page with the kind of vacation they want to have. “One of my favorite questions to ask,” says Nicole Martinez, a co-founder and chief design officer of Let’s Jetty, “is ‘What is everyone’s intentions for the trip?’” This gives members of your group the opportunity to share whether they’re looking to lounge beachside at an all-inclusive resort or want to hit the trails and camp. Then, get more granular: What experiences do you hope to prioritize on the trip itself? You might be open to spending more money on meals and museums, but want to stay in cheaper lodging and skip shopping. (More on how to handle these kinds of money conversations later.) Once everyone has shared their preferences, the group should ideally feel prepared for the type of vacation you’ll have. This includes whether the trip is child- or partner-friendly. Maybe a majority of the group is aligned in their desire to do wine tastings. Your toddler might not have the best time. Having this knowledge allows you to make a choice on whether to sit this one out. However, just because your friends want to do a ski trip doesn’t mean you necessarily have to skip as a noted ski-hater. Many ski resorts and towns offer other activities, like spas or shopping, for people who want to join the trip without partaking in the main activity, Martinez says. Talk about budget early on One of the biggest factors determining the type of trip you’ll have is budget. People often dance around the topic of money instead of offering concrete boundaries for what they can and can’t afford, says financial therapist Amanda Clayman. We say “I’d like to stay someplace nice, but not too fancy,” Clayman says, when we really mean “my budget is X amount a night.” To get around this, Clayman suggests saying to your friends, “It would be really helpful if we could all share what we’re comfortable spending on a hotel” or “What is everyone comfortable spending on dinners?” Get clarity on how you’ll split expenses. Maybe each person will pay for their travel and lodging individually. Set a deadline for when everyone will book and pay for any of these charges, Matta says, so one person isn’t saddled with the bill for an entire hotel stay when they were supposed to split it with four people who backed out of the trip at the last minute. Figure out how you’ll split any costs that the group incurs on the vacation itself. Maybe the person who wants to rack up credit card points will pay for activities and meals. How will you keep track of what everyone owes? Matta and Diep suggest bill-splitting apps like Splitwise or Tab for dividing up costs. Give your friends the flexibility to opt out of certain excursions or activities if they’re out of budget, and never force anyone to spend more than they’re comfortable with. If you do decide to upgrade certain experiences — like sitting in first class on a flight or choosing a more expensive hotel — be prepared for potential hurt feelings, Clayman says. “That comes down to the values of the friend group,” she says. “Is there a higher value on togetherness [or] the individual value on comfort?” Set expectations on how you’ll spend your time To address potential pain points like staying in separate hotels, be explicit with how much time you hope the group spends together. For example, if your ideal vacation includes eating, sleeping, and sightseeing with every travel buddy for the entirety of the trip, you may want to select lodging or activities that are in everyone’s budget in order to fulfill that goal. Let the group know how much time you expect to spend in smaller groups or on your own, too. Maybe you and another friend are early risers and plan on getting breakfast each day without the rest of your pals. If there are activities you hope everyone attends — like a group dinner — give the rest of the group a heads up, says Suzie Palma, a co-founder and chief product and growth officer at Let’s Jetty. You could say, “I made dinner reservations for all of us the last night of the trip. It would be awesome if we could all celebrate together.” Letting your friends know your expectations on togetherness gives them an idea of when they can peel off, too. Sometimes a friend just needs some alone time in the middle of the day and that’s okay. Palma advises against scheduling every part of your trip down to the hour, since it’s unlikely you’ll be able to hit every spot and you’ll end up feeling rushed. Instead, schedule one or two big activities for the day and fill in the gaps. Maybe you’ll book a surfing lesson in the morning and score tickets to a comedy show at night. What else is in the vicinity of those two locations that can keep you occupied during the rest of the day? You could opt for spontaneous wandering or refer to a collaborative Google Map where you all have flagged potentially interesting locations throughout your destination. “What are the things to do in that area?” Palma says. “Here’s the wine windows in Florence that we can check out while we’re going to this restaurant.” One friend might naturally take the lead in planning, but make sure each person has some input on the itinerary. Maybe everyone takes a turn planning a different day of the trip. Or the lead organizer can delegate tasks, such as asking one person to pick up firewood for the cabin. Just remember not to get upset if they don't do their homework, Matta says: This is supposed to be fun for everyone, not an obligation. If things don’t go quite according to plan, stay flexible, says travel agent Erionne Thompson. Try not to break down if your suggestion to whitewater raft is overruled or the restaurant you booked actually can’t accommodate you. “Come in with an open mind,” she says. “There may be things that others within the group may not want to do.” What to do if someone gets mad It’s entirely possible that someone might get frustrated, tired, or hangry and not be on their best behavior. The larger the group, the more likely clashes of personality are to occur, Matta says. Try not to let the tension escalate. If a friend isn’t acting like themselves, address the person individually and ask them if they want to talk about it, Thompson says. Whether your friend has an issue with another traveler or simply didn’t get good sleep, you don’t want to let animosity follow you home. Sometimes your friend may want space. Let them have it. The best-case scenario for any group trip is for everyone to enjoy themselves — and remain friends once you’re back home. Even if everyone’s vacation looks a little different, so long as you communicate and stay open-minded, everyone is bound to have a trip for the ages.