How a Week Aboard a Tiny Sailboat With Strangers in Croatia Became My Favorite Trip

Photo: Getty Images/Ryan Brown EyeEm
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Exactly 36 hours after a newish friend invited me to join her and a group of people I'd never met before on a weeklong sailing trip on the Adriatic Sea in Croatia, I was ready to go, with a plane ticket and everything. I'd met Sydney, the friend who invited me, the year before at a wedding and knew she and a bunch of her Italian friends embark on an annual sailing trip to various destinations. This year though, the group ended up being a crew member short. My general travel (and life) philosophy is to jump at new opportunities. So, although Croatia was low on my travel bucket list, I knew nothing about sailing, and wasn't necessarily keen on traveling with strangers, giving that immediate "yes" RSVP was a no-brainer. It wasn’t until the tickets were booked that I started backpedaling….

“Wait, this boat looks pretty small—are we sharing that minuscule-looking closet as a bedroom?” I asked Sydney.

“Yes,” she said.

“Will we be bored just floating around all day long without wifi or any distractions? Will we get seasick?”


“What if we don’t all get along and it’s super awkward and there’s nowhere to escape! It’s two couples and us—is that weird?!”

“Bring a good book.”

“Wait, it’s SEVEN days? I thought it was only five. Crap, I read the text wrong…this is a long time to spend traveling with strangers in the middle of the ocean!”

Luckily, excitement won out over my momentary panic, and upon meeting the group on a dock in the coastal city of Split, I knew my gut instinct was right: This was going to be great. Fabio and Davide introduced themselves as the most experienced sailors, and Fabio would play captain. Their respective girlfriends, Eugenie and Gabri, would practice their amateur sailing skills as skippers.

We soon realized French and English were our common languages and began ping-ponging between the two. Their imperfect English put me at ease practicing my imperfect French. The immediate, palpable vibe of openness and acceptance among the six of us shocked me, and whether it took hold because we knew we’d be spending so much time in close quarters or thanks to the humble disposition of each person, I'd never know. What I did know is that I felt refreshingly recognized among this group of friends who were already so comfortable among each other.

And these weren't wallflowers, either. For the first four hours at sea, they peppered me with questions about my life in New York. After all, as foreign as they all were to me, for them, I was the wild card on this intimate excursion.

In another setting, perhaps this same group would have resisted sharing thoughts so personal and specific, but I'll be forever grateful for what turned out to be a mini yet enduring spiritual journey.

As soon as we docked at Isola di Solta for the evening, the sun began to dip toward the horizon. Refreshed and suddenly starving, we pulled together a full aperitivo spread to devour onboard—with thoughtful considerations made for Sydney and my dietary requests. (Before the trip, she alerted the group that the two of us avoid dairy and gluten, and as we unloaded the groceries, Gabri and Eugenie pointed out the “safe” alternatives they purchased. So, kind, right?) The small act of ensuring that each of us had enough to eat became an enduring means of showing kindness.

Quickly, we settled into a routine that made our ship feel like a tiny, sustainable community: We rotated doing wash dishes, meal-prepping, and taking out the trash. In the mornings, Sydney led meditations on the bow of the boat, and I offered tips for staying centered and techniques to bring back home.

We were already proving to be an exemplary crew, but the group dynamic tightened further when Sydney suggested we play The New York Times’ 36 Questions that Lead to Love, a list of questions designed to illicit deeper knowledge and promote bonding. As we sat around after dinner, exchanging childhood stories, lessons learned, and embarrassing moments, we decided to choose one question from the list, and each person was to provide a two-minute answer.

Question one was “What does your perfect day look like?” Answers included "Tiramisu made by my mom" and  "And it’s my birthday” and “Lots of sex…really, so much sex.” The next time we played, the prompt was “Explain your life story in four minutes.” This revealed facets of each person's respective history that may normally haven taken months to extract from a new friend.

Toward the end of our trip, we hiked up the island of Lastovo for a sunset aperitivo and did an activity Sydney learned at Summit Mountain Series. In groups of three, two people would simultaneously whisper affirmations into the ears of third person. The idea here is that when both ears receive different messages, the hemispheres of your brain are trained to absorb without judgment. Hearing statements like “you have a sense of calm about you that makes people feel comfortable,” “I see the way you care for your partner’s needs and she appreciates it more than you know,” or “I know you have been through a lot this year and I’m inspired by your optimism,” brought about strong hugs and even a few tears. In another setting, perhaps this same group would have resisted sharing thoughts so personal and specific, but I'll be forever grateful for what turned out to be a mini yet enduring spiritual journey.

When I got home to my Manhattan studio apartment, I felt full. I wondered what my new friends were doing at that very moment and when we’d see each other again. I teared up and thanked my lucky stars I had said yes on a whim to that initial invitation to spend a week traveling with strangers. And, to this day, when people ask me “How was Croatia?” I answer that it was one of the best trips of my life—not because of the destination or even the journey, but because of the people.

If traveling with strangers isn't quite your speed, check out why one writer says the best way to see the Greek Islands is to run to the top of them. And why getting injured in Hawaii was actually a blessing in disguise for her trip and her body.

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