Words: Ashley Hart

I’ll never forget my first time in St. Vincent and the Grenadines. More than 30 years ago, I was just 14 years old when my parents told me they had chartered a small sailboat in a southern Caribbean country that I knew nothing about. I’d been lucky enough to spend time in other parts of the Caribbean but nothing had prepared me for this one-of-a-kind place.

When we arrived, we were greeted by our Captain, James, and his golden retriever, Wiz, who would be our skipper and first mate for the week. Tom had a weathered look about him, gained, earned from 15 years of sailing up and down the Grenadines. As such, he knew the water like the back of his hand. He guided us through impossibly turquoise waters, taking us to islands with distinctly different vibes and introducing us to locals who were always happy to welcome us and make sure we were fed a proper amount of fresh, local seafood. 

St. Vincent and the Grenadines is a chain of 32 islands, of which only nine are inhabited. The archipelago is pristine and the marine life thrives here. We bounced around a number of places and for the latter half of our trip, we dropped anchor at the marine park in the Tobago Cays where my brother and I would spend the days snorkeling with sea turtles and the evenings listening to Captain James share tales from his  years on the water. We were in absolute awe. The week flew by in what felt like an instant but it left an undeniable impression on me that would ultimately change the course of my life. 

Growing up in Rhode island, my love for sailing began at a young age. My family had taken trips to various sailing destinations over the years but following our first trip to the Grenadines, there would never be a year that I didn’t return to the Southern Caribbean. When I turned 20, my brother and I began venturing down on our own, renting small sailboats and cruising between the islands of St. Vincent, Bequia and Mustique—which my family had honed in on as an annual destination. Every year was a new adventure, but always included familiar faces as we forged lifelong friendships with the people we met along the way.

When most people think about cruising in the tropics, they picture the British Virgin Islands with polished resorts and beach bars buzzing with expats. But it’s different here—the islands are full of the friendly, laid-back locals that grew up on them. With a resistance to overdevelopment, St. Vincent and the Grenadines exudes an authentic Caribbean feel that you simply can’t find anywhere else. 

Fast forward to 2018, when I was on a sailing trip with friends and we anchored our catamaran in Salt Whistle Bay, Mayreau. A stunning sight to behold, the white sand is lined with palm trees and the beach stretches all the way around the horseshoe bay, as if pulled straight from a postcard. It’s an absolute must-see on any trip and we always made a point to stop here and visit our friends BB and Debbie, who run a BBQ on the beach. 

One day, during a massive rainstorm, I went ashore to spend time with them and we sat together for hours, playing music and sharing stories. On that night, laughing with friends as it poured outside the thatch-roofed shack, I had a realization: this is how I want to spend the best years of my life—bringing incredible people and beautiful music together in this utopia. 

Indeed, the idea of Rhythm & Sails was born that night but it would be a number of years before it would come to fruition. After a feverish stretch of planning conversations, a group of friends and musicians had rallied together for the inaugural voyage but just then, COVID struck. Like everybody else, we were forced to let our plans simmer, but we didn’t lose hope.

As the world began to reopen to travel in 2021, we gathered our crew of 31 souls and headed south. Customs told us we were the very first flotilla to sail through the country after the pandemic and, taking all necessary precautions, we brought the vision to life. Sailing catamarans from one beautiful island to the next, playing and listening to music under the stars, and dancing with friends new and old—it was even better than I could've imagined. It was pure magic.

The group of friends that set sail on that first trip now serve as the majority of the Rhythm & Sails crew—and we're damn lucky to have them on board. Every one of them embodies the very spirit that this company was founded upon and revels in sharing that same feeling with our guests. As we get ready to embark upon our sixth year of operation, we invite you to come and meet them for yourself, lean into the experince and see what that magic is all about.