A first-timer's guide to pulling off a multi-family trip

Spring break trips were always something our family talked about, but the idea of crowded peak-season travel and high prices always kept us home.

Until this year, when finally the time had come to get going. And if you’re wondering how to make an already-complicated trip with three kids even more complicated, I’ll tell you the secret: Add two other families to the mix.

Sure, we were excited. Friends for the kids meant more time for the adults to actually relax (not always a possibility when you’re vacationing as a parent). But even among my own kids—8, 13, and 16—there would be challenges: The youngest two love animals and adventures, whereas the oldest would be happy with shopping and beach time. So where could we go that would be fun with an even larger crew—of 12? Where would we stay? What would we do? Would we survive?

Cut to the end: After 11 nights, two Costa Rica destinations (Tamarindo and La Fortuna), and one jam-packed passenger van that teetered as it heaved along, I’m here to report that we survived, yes, and we had a blast. Here’s what I learned along the way:

We all agreed that Hawaii was “overdone.” A European escape might be too much walking for the youngest kids. And the dads didn’t want to lie on a beach all day (sorry, Mexico all-inclusive).

By the time we had triangulated each family’s individual criteria over a beer-swigging dinner, we landed on Costa Rica. It offered a solid balance of beach-bum-iness and outdoor adventure, diverse culture, and great eating, plus a range of places to stay. From there, we decided to divide our trip in two: a week in Tamarindo (a bustling beach town on the Pacific coast), followed by five days in La Fortuna (a rugged rainforest region further inland).

Every party needs a planner. Luckily for our group, that task fell to another mom, who regularly organized trips with a full arsenal of organizational methods to draw from, including spreadsheets and packing lists. A shared document, begun well in advance, allowed us to track some potential things to do and log our individual interests. When it came time to plan some small-group activities and excursions, we used that list to assess the themes and overlaps.

We also used the list like a checklist, adding our names under each prospective activity to indicate interest. From there, we were able to delegate duties, deciding what needed to be pre-booked in advance; for example, a ziplining excursion as well as that aforementioned van.

In Costa Rica, it’s often the case that two things you want to see are a great distance apart and difficult to access without a car. Driving also helped our group keep costs at bay.

Space was tight in our 12-passenger Nissan Urvan, but we loaded up on snacks, swapped stories (many of which focused on embarrassing the parents), and even sang along to old radio tracks that played—that is, while we had service. Good ol’ Urvan took us here, there, and everywhere, and the hilarity that ensued while we bumped along Costa Rica backroads is among the things I’ll remember most about the trip.

As for who claimed the “chauffeur” shifts: That came down to who could drive stick—thankfully, enough of us had enough experience on that front.

We wanted to be close, but not too close: That’s why we settled on accommodations that offered ample room. In Tamarindo, that meant three different condo rentals in the same building. We all had access to the shared amenities (like a pool) and were able to easily coordinate the day. But each family also had enough privacy: Kitchens for midday snacks and bedrooms for shaded snoozes made it easy to take quiet time-outs without things getting weird. And who doesn't love a good private bathroom?

At our second stop, in La Fortuna, we switched things a bit, giving the older teenagers (themselves best friends) their own hotel room. They took it as a welcome break from their annoying parents and little siblings and a great way to enjoy a little independence—but this mom knew they would never be too far.

There’s no restaurant on earth that will please everyone; you’re sure to run into disagreements large and small about activities, too. But hey, all good. To solve for this, we incorporated several small-group excursions—horseback riding for some, ziplining for others. Some of us preferred to hang back and sunbathe by the pool; others were excited about a full-day fishing trip. Some were into nearby late-night rodeo; others were content hitting the sack early (and probing for rodeo details about the next morning at breakfast).

But that’s the thing: We found that the more we allowed each other our space, the more we enjoyed the moments together. And that, perhaps, was the whole point of the trip to begin with.