The Ultimate Way to Bond With Friends? A Private, Over-the-Top Caribbean Island

How a travel writer turned a milestone birthday into an unforgettable group retreat at Moskito Island in the Caribbean.

 Aerial view of one person standing in circular pool next to coast of island

A pool on Moskito Island in the Caribbean

Courtesy of Moskito Island

I’m a travel writer, and for the last dozen or so years I’ve spent much of my life traversing the globe, frequently solo. I’ve been on the road more of every year than I’ve been home, global pandemic notwithstanding. In that time I’ve missed weddings, anniversaries, births, deaths, and holidays. I’ve spent my own birthday wrapped up in aloneness catching flights filled with people. That’s the job sometimes.

The people in my life have come to expect wild stories and tales of far-flung locales. Some of them have occasionally rendezvoused with me, swinging through a weekend stay at the Oberoi in Marrakech, accompanying me on a wellness-focused weeklong road trip through Arizona, gallivanting across Ibiza. Even so, I grapple with the issue of being a good friend. Everyone loses track of where I am in the world, and it’s inevitable that I’ll respond hours late to a text message. Sometimes, when the simple act of sitting on my couch with a friend is all I want, I’ll find myself 15 time zones away from that reality.


I had never intentionally planned a trip to a distant locale with a group of my closest friends. That is, until I faced a milestone birthday; confronting some of the realities of the friendships in my life, I wondered whether I could maintain them better. Through a few work connections, I had a chance to book a group stay in some of the newly renovated villas on Moskito Island, the private Caribbean paradise Sir Richard Branson bought in 2007. Could this be the friendship-building opportunity I was seeking?

The invite was a bit bananas: ask a dozen or so friends to fly to the British Virgin Islands and be whisked via a 42-foot power boat to Moskito Island for a six-day, five-night extravaganza, including a golf cart-fueled scavenger hunt, Hobie Cat races, nightly themed dinners, morning hikes, and yoga classes. The only person who knew everyone in attendance was me, and to my surprise, 11 very busy people in my life said yes. Many of the yeses came with a note or comment echoing my cravings for face-to-face time with like-minded humans somewhere completely outside of their everyday lives.

A white hilltop bedroom on Moskito Island, with four-poster bed and open to large wooden veranda

A hilltop bedroom on Moskito Island

Courtesy of Moskito Island

We’re not alone: Recent surveys have found that about half of U.S. adults report experiencing loneliness, with the highest rates among young adults, according to a 2023 report published by the U.S. Surgeon General entitled Our Epidemic of Loneliness and Isolation. Meanwhile, in a 2022 report, The Global State of Social Connections, Meta and Gallup examined feelings of connectedness and loneliness among people from 142 countries. “The degree to which social needs are fulfilled—or not—impacts the health, well-being and resilience of people everywhere,” the report reads. It seemed my friends and I were all collectively counting on this milestone birthday trip to recharge our depleted social batteries.

Moskito Island has four luxury private estates; each can accommodate about two dozen guests. Set amid 132 acres of tropical forest and buttressed by sandy beaches, our retreat was composed of contemporary cliffside cottages, an in-house chef and at-the ready bartender and barista, an abundance of pools, and an incredible staff available for any kind of request.

During the trip, an easy familiarity quickly fell over the group. One afternoon, we dined on fresh local sashimi and handrolls placed in a white cotton-wrapped, ice-filled kayak floating in the 180-foot infinity pool at the Point, a three-acre property with eight suites, a crow’s nest lounge, and a Balinese-style seaside pavilion. There, I took delight in watching my friends of different backgrounds find common footing. Amy, a musical theater loving, Texas born-and-bred banker and mother of two, connected with Katy, a Formula 1 obsessed, former foreign service officer cum oyster farmer, over a mutual passion for snorkeling. On one evening, a themed dinner requested that we dress up as our favorite literary hero on vacation, and my friends James and Teresa showed up as the same character—Hunter S. Thompson—triggering waves of laughter.

The writer, second from the right, and three friends on a boat, with sea and Moskito Island in background

Moskito Island is a playground of beaches, water, and green jungles.

Courtesy of Moskito Island

On another windy day during golden hour, we house hopped from the Point to the newly opened Cape Stout, another estate near where we were staying, and sampled the three bars with beer on tap, four pools, and trio of Jacuzzis. Conversations among my friends led to our definitions of success and our own perceived failures in prioritizing friendship. I was not the only one who cried.

As much as I felt a kinship with everyone, I found myself seeking out solitary moments—an old habit, I suppose. And then I’d hear my friend Sara’s booming laugh, or Joe’s thundering cannonballs into the pool, and I’d be drawn back into the fold, eager to exchange a hug or a high-five. It was that rare feeling of community, away from the daily grind and in an impossibly idyllic setting, that I’d use to fill my emotional cup during my subsequent solo trips, and one so rewarding that my friends and I are already scheming our next escape.

Alexandra Cheney is travel writer, culture reporter, and luxury brand consultant based in Los Angeles. She can usually be found on a surfboard, on an airplane, or on deadline. Her work regularly appears in the New York Times, Robb Report, Elite Traveler, and Luxury Magazine.
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