Your Guide to Planning a Family Vacation with Friends

A study from HomeAway and FamilyFun found that more families want to vacation with friends! Here’s how to plan an awesome group trip.

Kids Running Cruise Vacation Alena Ozerova/Shutterstock

As soon as Kristin Liskow booked her family’s February 2017 vacation in Playa del Carmen, Mexico, it hit her: The trip would be even more epic with family friends. So she passed along the details to a few close buddies. She lobbied them. She cajoled them. Soon, another family opted to tag along.

It ended up being one of the Liskow family’s best vacations ever.

“Traveling with friends provided built-in playmates for my husband and me, as well as our 3-year-old,” says the special-education teacher from East Northport, NY. “Being with good friends makes every aspect of a trip more social—and more fun.”

The Liskows are on to something. Anecdotal evidence from travel experts suggests that group travel is a growing trend. Data from a recent survey HomeAway conducted with FamilyFun backs this up too—74 percent of respondents said they want people outside their immediate families on vacation with them. 

But how do you make these trips work? After all, there are challenges along with the opportunities. Our advice will help make sure everyone comes home as close as (or closer than) before you left. 

Make Good Choices

Perhaps the most important decisions about a vacation with family friends come in the planning stages, when you’re deciding where to go and whom to go with. Some families, including the Liskows, make the destination the main point, inviting friends only after they set up an itinerary. Others prioritize the traveling companions, then decide on a destination together.

Chez Chesak, executive director of the Family Travel Association, says both approaches can work. For first-timers, it’s usually easiest if one person lays out the trip’s framework and then opens it up to friends to join. Then, for the next trip—when you know you guys travel well together!—you can plan it in tandem from the beginning. 

Set Expectations

Once you’ve selected your destination and companions, the next step is booking accommodations. While vacation rentals generally mean more space than hotel rooms, they also require more buy-in when it comes to cooking and cleaning. Amie O’Shaughnessy, CEO of Ciao Bambino, an online family-travel resource and Virtuoso travel agency based in San Francisco, suggests that having a conversation about these options will make it easier to choose one that appeals to everyone, and will create an opportunity to come up with a strategy for who does what once you’re there.

“The only way you’re going to know what your traveling partners are expecting is if you ask them,” O’Shaughnessy says. “In some cases, coming up with a schedule beforehand actually might be the best approach.” Along these lines, it also might pay to discuss finances and establish a daily budget for groceries and activities. 

Stake a Claim

Another issue to resolve: who’s sleeping where. Whether you are sharing a rental or splitting hotel rooms, it’s important to decide whether each family will stay together, or if you’ll split up. If you’re considering letting the kids bunk together, remember this: Sleepovers often lead to sleep deprivation, which can curtail daytime fun.

For families sharing a rental house, divvying up bedrooms also can get dicey. Chesak says one way to address this is to assign every bedroom a value based on square footage or amenities (bathroom, deck, view, etc.) and have each family pay for what they use. Another option, especially when the house has, say, an awesome master bedroom, is to switch halfway through the trip so everyone gets a turn. “The goal is fairness,” he says.

O’Shaughnessy adds that for families with children who have special needs, or those that just want their own space, the best move might be to get their own accommodations nearby. In the case of a hotel, perhaps this means a separate room down the hall; in the case of a rental, it could mean the in-law unit of a larger house. 

Establish a Schedule

One of the best aspects of vacationing with family friends is that the group can split up so people can do their own thing. While this freedom is invigorating, it also can divide the group if left unchecked.

One way to combat this is to set up a daily schedule. Erika Lenkert, an entrepreneur from San Rafael, CA, did this on a four-family, 14-person trip to Barcelona this summer. No matter what they did during the day, everyone agreed to return at the same time every night for a group dinner. The meals quickly became a focal point of the experience. “The city was amazing, but dining at a big table with all of our friends was amazing too,” she says. 

Navigate Drama

Unfortunately, you’re probably going to run into at least a little drama with group travel. So be prepared. In general, the best way to troubleshoot is to give it space. Lenkert says this is how she handled these situations on her multifamily trip to Barcelona. On the rare occasion when one or more travelers weren’t seeing eye-to-eye, each simply took an outing on his own, giving everyone the opportunity to reload their patience.

Follow Your Truth

The last tip for planning a successful vacation with friends is perhaps the toughest one: Be true to your family’s individual mission. Some days, everybody in the group will be interested in doing the same activity. Other days, it will feel like herding cats, and it’s up to you to be proactive about doing what you want.

According to Liskow, this approach guarantees the best of both worlds—an exciting vacation for your immediate family, highlighted by shared experiences with friends. “This kind of travel works best when everybody’s doing what they want,” she says. “It’s fun to have new adventures with friends, but at the end of the day, it’s still your vacation.”