How to Vacation with Another Family … And Stay Friends

As an only child, my son loves it when we travel with other families. Having additional kids along for the trip is infinitely more fun for him than hanging out with Mom and Dad. Likewise, my husband and I love having the chance to spend time and make memories with friends in a new place, free from all the commitments, comings and goings of our busy day-to-day lives.

That said, a successful multifamily vacation doesn’t just happen; it takes intensive input and work on the front end to ensure that your friendship survives intact. We all know families who have boarded a plane or hit the highway together in jovial spirits and with high hopes — only to return home simmering with resentment and barely on speaking terms. Don’t let this be you.

Tips for a Successful Family Vacation with Friends

Choose travel friends wisely.

A good friend at home does not necessarily translate to a good vacation partner. You’ll be spending a lot (a lot) of time together on the road, so think about your respective travel styles, parenting styles, comfort level with each other, introvert/extrovert tendencies and similar considerations before you take the plunge. If your family likes to rough it while the other prefers 5-star luxury, or if you’re a hardcore planner while your friends fly by the seats of their pants, you might not be a match. And no matter how much you enjoy another couple’s company, if your kids don’t get along well with theirs, the trip will go south fast.

Start planning well in advance.

With two families or more, the logistics multiply exponentially. If you all want to book the same flights and stay in the same hotels, secure those early in the game — ideally, six to 12 months out, depending on where you’re headed and how popular it is at that time of year. If you’re renting cars, decide whether you’ll want a separate one for each family or a van that can hold the whole gang. Know too that many private guides will only accept groups of up to six or seven, and tours may have a size limit. The more time you have, the more options you can pursue.

Decide how you’ll split costs.

It doesn’t really matter how or when you settle up as long as it works for all concerned. For example, I’m usually in charge of arranging everyone’s accommodations, so I’ll book with our family’s credit card and get reimbursed afterward. Other families might prefer to book everything independently. In a similar vein, agree on how to pay for meals and incidentals as you go (splitting the check versus alternating).

Book accommodations that give everyone some space.

One of the keys to a successful multifamily trip is not feeling like you’re on top of each other. When we travel with friends, each family has their own accommodations (sometimes different rooms in the same hotel; more often, rental apartments) which allows us all plenty of privacy, room to spread out and alone time when we need it. If your group would rather stay together in a large villa or other property, pick one that offers ample sleeping space, outdoor areas for the kids to blow off steam and a spot where people can retreat on their own.

Work out a plan for mealtimes.

Do you want to eat every meal out, or do you want accommodations with a kitchen? If it’s the latter, is one person in charge of the cooking, or will you take turns? Set clear expectations at the outset so no one is left grumbling. Kids can have very different meal schedules and preferences, especially if there’s a wide age gap, so factor that in as well.

Let each person choose a few things to do.

This is the fun part! Take turns adding ideas to the wish list, and include the kids in the process. Art museums, soccer matches, historical monuments, cooking classes — everyone gets a say. It’s a great opportunity to experience local sights and activities you might not have chosen, but that will end up being some of your favorite memories. And who knows? You or your kids might even discover a new interest that will last far beyond the trip.

By the same token, be flexible when plans go off the rails. Transport delays, unexpected closures, multiple snack breaks, meltdowns … they’re all part and parcel of family travel. Don’t let them ruin a precious day of vacation; just do what you can to adapt, adjust and move on. Some of our most priceless photo ops and best stories have come about from snafus.

Set boundaries for electronics and social media usage.

Be clear on when and for how long the kids are allowed to use their devices, message friends back home, post on social media and more. Families typically have varying rules about screen time, but meeting in the middle keeps the peace. If one family isn’t comfortable being tagged and having photos of themselves shared on Facebook or Instagram, honor their wishes and make sure your kids do the same.

Divide and conquer when necessary.

It’s OK to split up now and then — you don’t have to move in lockstep. During a stay in Tuscany with friends, my husband and son were gung-ho to see the Leaning Tower of Pisa one afternoon while the rest of us just needed a nap by the pool. We all did our thing, and everyone was happy. The more flexible and accommodating you are, the more seamless and enjoyable your vacation will be.

Cut each other some slack.

Family travel is magical — and stressful. Just about every person in your group, kids and adults alike, will have a moment or a day of feeling cranky, tired, “hangry” or otherwise less than their best. Let it slide and, in turn, you’ll appreciate it when they do the same for you.

Relevant Links:

Browse all family travel tips on Ciao Bambino

What we wish we’d known: 31 essential family travel tips from the CB! staff

How family travel creates resilient kids

Tips to make multigenerational travel fun for all

Tips for healthy travel with kids

8 ways to reduce stress when flying with kids

Editor’s Note: Photo by Natalie Ethridge.