I Traveled to Costa Rica With 17 Family Members — Here's How We Pulled It Off

Have you ever wondered what it would be like to go on vacation with nearly 20 family members? I have the answer.

If you’ve ever traveled to Costa Rica, you’ve likely heard the term pura vida, a country-wide phrase that translates to “pure life” or “simple life.” But anyone who has ever tried to plan a trip with almost 20 people knows there’s rarely anything simple about it.

It was last November when 17 of my closest relatives sat around a dinner table and decided another family trip was in order. With family members ranging from three to 60 years old, and spanning New York to Pennsylvania to Colorado, this would be our first vacation back together again and after the passing of both my grandparents.

While the prospect of such a large group getaway might sound daunting, with a bit of help, we were able to create a memorable trip of a lifetime. Here are some of the tips and tricks that helped us along the way.

One key to our success, especially in the early stages of planning, was having one main decision-making point person. For us, that was uncle Frank. Everyone shared their individual family needs and desires; then, he took that information and ran with it. This way, there weren’t more than a dozen people trying to communicate and plan.

It’s also important to establish even the most basic ground rules before leaving. In our case, since we were joining three fairly widespread families, that meant making sure everyone knew and agreed on the schedule so there was no confusion before taking off. Communication is a must for any successful trip, but especially when dealing with a group of our size.

Sometimes, the best tricks can often be the smallest. Ensuring the whole group had TSA PreCheck, for example, helped us fly through the airport. When traveling with nearly 20 people, that’s an immeasurable commodity.

Be sure to pack a good pair of soundproof headphones and an AirFly Pro, too, so you don’t need to leave your fate to a pair of in-flight earbuds. Pop those on, along with an eye mask, and it will make the noise emanating from the four full rows of family members sitting behind you simply melt away — at least for a few hours or until the snack cart comes around.

Asking for help when necessary was also vital to our trip's success. Tagging in a travel agency and accepting help from the incredible staff at Dreams Las Mareas was paramount. Fort Hill Travel planned and booked our stay and airfare, and organized a bus big enough to fit the whole family plus 18 carry-on bags and 21 pieces of checked luggage.

My uncle, the point person, shared the parameters of our trip with our travel agent and they provided options for a few different countries, resorts, and flights within our budget. We knew Costa Rica and Dreams Las Mareas would be the perfect backdrop for a trip this special.

One must for our trip was an all-inclusive resort. It was the best way to help with the group’s individual budgets, as well as ensure everyone gets the most out of their stay. With food and drink baked into the price of the stay, the all-inclusive resort eliminated day-to-day stress of doing things like making dinner plans for 18 people. The unlimited passion fruit mojitos didn’t hurt, either.

At Dreams, there are plenty of activities such as cooking classes, sunset kayaking, and sunset and morning hikes. There’s also an on-site waterslide, which the adults enjoyed just as much as the three-year-old. I recommend talking to someone at the resort for the best and worst times for a party of your size to sit down for dinner. We were told anything later than 7 p.m. would be difficult to accommodate, given our group size. Having those quick conversations allowed us to enjoy every meal together.

It’s also crucial to understand everyone has a different vacation style and respect that on a family trip. Knowing each other’s needs and deciding to split off when necessary allowed us to accommodate individual interests and preferences while still enjoying family time. One day, 14 of us explored Buena Vista del Rincón, hiking to waterfalls, soaking in hot springs, zip lining, and horseback riding. The remaining four group members spent their day happily lounging by the resort’s pool, and we all met up for dinner. That said, we all spent most days lounging and laughing by the pool together, including one very intense game of Monkey in the Middle. Though it can be viewed as a vacation faux pas to wake early and reserve your spot by the pool, I recommend asking a few resort employees to help set up your lounge chairs so your family can stick together, especially when dealing with a large group.

If you’re like me, you’ll wind up being the family photographer. To give yourself a little peace, I recommend iPhone users create a group chat and shared family photo drive. It’s the easiest, stress-free way to distribute photos during and after a trip. It’s also the best way to find 55 photos of the adorable capuchin monkeys that climbed all over the resort's terraces. In our shared album, you’d find incredible Costa Rican sunsets, three not-so-great full family photos, and three-year-old sister eating corn on the cob for breakfast

Lastly, it’s important to take some time for yourself on family trips no matter the size of your group. Whether it’s getting a treatment at the resort spa, enjoying a quiet moment with a good book, or napping by the pool (or terrace hot tub or swim-up pool, if you have a preferred status at Dreams), carving out a bit of relaxing self-care time is essential for recharging and enjoying the rest of the trip with your brood. Don’t be afraid or feel guilty if you need to close that adjoining room door.

Ultimately, the best trick for pulling off a family trip of this magnitude is to soak in the little things. It’s in those small, sometimes quiet (or, if you’re my family, loud) moments where the real magic happens. It makes the chaos of attempting to pack 18 people, including a toddler, and 40 pieces of luggage into a single van that needs to traverse a winding, dirt road completely manageable. If you do this, you’ll be left with only good feelings. Feelings of recognizing how special the last few days have been. You’ll cherish every watermelon mimosa you toasted with and realize how much better they tasted because you experienced them together.

I also recommend checking in on your family group chat the morning after you return home. You’ll all need a little cheering up and perhaps even start planning a follow-up family adventure. Next up, we’re thinking of getting 20 people on a flight to Thailand.

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