Wendy Diep thought all her friends were on the same page when she booked a trip to Disney World and Universal Studios in Orlando a few years ago: Roller coasters were definitely on the itinerary. He was unfortunately wrong.
“One girl never rode a roller coaster, and everyone wanted to ride a roller coaster,” says Diep, co-founder and CEO of the group travel planning app. Let’s go. “We had to assign someone to hang out with her because she didn’t want to be alone.”
Mismatched expectations are one of the many ways vacationing with a group of friends can happen. When you’re traveling, you’re faced with dozens of decisions that you don’t always have to make in your everyday life, says Auston Matta, owner, founder and CEO of travel advice and LGBTQ group trip planning website. Two bad tourists. A group of friends can often have conflicting ideas about where to eat, what to see, how much to spend and how to get around. Add the stress of living in a new place and disagreements are bound to arise.
But you don’t have to bar the possibility of conflict from jet-setting with your friends. Most of the planning and discussion should be done before you pack your bags. What experts say is to make your friend as pain-free as possible.
First, figure out what type of trip you’ll be taking
Group trips usually come together in one of two ways, Matta says: One friend decides on a destination and takes the others, or a few people commit to traveling together and they collectively choose a locale. Regardless of how the idea originates, everyone should be on the same page about the type of vacation they want to have.
“One of my favorite questions I get asked is, ‘What’s everyone’s purpose for the trip?’” says Nicole Martinez, co-founder and chief design officer of Let’s Jetty. Looking to lounge at the resort or hit the trails and camp.
Then, get more granular: What experiences do you hope to prioritize on the trip? You may be open to spending more money on food and museums, but want to stay in cheap accommodations and skip the 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 will have. This includes whether the trip is child- or partner-friendly. Maybe most of the group is united by their desire to go wine tasting. Your child may not have the best time. Having this knowledge allows you to choose whether to sit it out or not.
However, just because your friends want to go on a ski trip doesn’t mean you have to be shunned as a famous ski-hater. Many ski resorts and towns offer other activities, such as spas or shopping, for those who want to add to the trip without participating in the main activity, Martinez said.
Talk about a budget early on
One of the biggest factors in determining your travel style is budget. Financial therapists say people often dance around the topic of money, instead of setting clear boundaries for what they can and can’t do. Amanda Clayman. We say “I want to stay somewhere nice, but not too fancy,” Clayman says, when what we really mean is “My budget is X amount a night.”
To get around this, Clayman suggests asking your friends, “It would be really helpful if we could all share what we’re comfortable spending on a hotel” or “What’s everyone comfortable spending on dinner?”
Get clarity on how you will share expenses. Each person may pay for their travel and accommodation separately. Set a deadline for when everyone will book and pay for which of these charges, Matta says, so one person isn’t saddled with the bill for an entire hotel stay when they’re supposed to be splitting it with four other people returning from the trip. At the last minute.
Figure out how you’ll split any expenses on the group vacation. Maybe the person wanting 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 to split expenses.
Give your friends the flexibility to opt out of certain trips or activities if they’re out of budget, and don’t force anyone to spend more than they can afford. If you decide to upgrade some experiences — like sitting in first class on a flight or opting for a more expensive hotel — be prepared for possible hurt feelings, Clayman says. “It comes down to the values of the friend group,” she says. “Together has a high value [or] Individual value on convenience?”
Set expectations on how you spend your time
To address potential pain points like staying in separate hotels, make it clear how much time the group expects to spend together. For example, if your ideal vacation includes eating, sleeping, and sightseeing with each travel buddy for the entirety of the trip, you may want to select accommodations or activities to meet those goals that are within everyone’s budget.
Let the group know how much time you want to spend in small groups or on your own. Maybe you and another friend plan to have breakfast every day without the early risers and the rest of your friends. If there’s an activity you expect everyone to attend — like a group dinner — let the rest of the group know, says Suzy Palma, co-founder and chief product and growth officer at Let’s Jetty. You can say, “I made dinner reservations for all of us on the last night of the trip. It would be nice if we could all celebrate together.” Letting your friends know your expectations about getting together gives them an idea of when to peel off, too. Sometimes a friend needs some alone time in the middle of the day, and that’s okay.
Palma advises against timing each part of your trip in hours, since it’s unlikely you’ll be able to hit every spot and you’ll feel rushed. Instead, schedule one or two big activities for the day and fill in the blanks. Maybe you book a surfing lesson in the morning and tickets to a comedy show at night. What else is around these two locations to keep you occupied for the rest of the day? You can choose to self-navigate or refer to a companion Google Maps where you’ve all flagged potentially interesting locations throughout your destination. “What to do in that area?” Palma said. “This is the wine window of Florence that we can see when we visit this restaurant.”
A friend can naturally take the lead in planning, but make sure each person has some input into the itinerary. Maybe everyone goes around planning a different day of travel. Or the chief organizer may delegate tasks, such as asking one person to gather firewood for the cabin. Just remember not to get upset if they don’t do their homework, Mata says: It’s supposed to be fun for everyone, not an obligation.
Be flexible if things don’t go according to plan, travel agents say Erion Thompson. Try not to panic if your advice on whitewater rafting is canceled or the restaurant you booked can’t actually accommodate you. “Come with an open mind,” she says. “There may be things others in the group don’t want to do.”
What to do when someone goes crazy
It is entirely possible that someone may be frustrated, tired or angry and not be on their best behavior. The larger the group, the greater the potential for personality clashes, Matta says.
Try not to let the tension build up. If a friend isn’t behaving like they are, approach the person individually and ask them if they want to talk about it, Thompson says. Whether your friend has a problem with another traveler or isn’t sleeping well, you don’t want to let animosity carry over into your home. Sometimes your friend may ask for space. They have it.
The best view for any group trip is for everyone to enjoy themselves – and stay friends after you get home. Even if everyone’s vacation looks a little different, as long as you communicate and keep an open mind, there’s bound to be a trip for everyone’s age.
