An 8-day Sailing Trip to This Part of the Caribbean Became My Family’s Most Adventurous Trip Yet

It didn’t take long to figure out why St. Vincent and the Grenadines — a dreamy chain of 32 sparsely populated islands in the southern Caribbean — is known for some of the world’s most challenging sailing. On the second day of our crewed charter, my family and I embarked on an eight-hour journey from Marigot Bay, St. Lucia, to Bequia, the Grenadines’ second-largest island. In no time, our 45-foot catamaran was cruising through eight- to 10-foot swells. Our captain, a six-foot-three St. Lucian named Johan Gangardine, explained that on a scale of one to 10, these seas were a five. “When the Atlantic and the Caribbean converge,” he said, “it’s like a whirlpool.”

As St. Lucia’s mighty Pitons began to disappear into a misty haze, the seas fell calm. We had lost sight of land, as often happens in this part of the Caribbean, and we regrouped aft to take in the vast beauty of it all. Bottlenose dolphins jumped alongside the boat, white-bellied boobies darted for their catch, and hardware clanked as ropes blew in the stiff breeze. 

We sailed past sprawling St. Vincent, covered in verdant peaks, cloud forests, and a stratovolcano that last erupted in 2021, before anchoring off Mount Wynne Beach, a secluded slice of black volcanic sand, the grains of which resembled caviar. That afternoon, we continued on to Bequia, where we stopped at Princess Margaret Beach, one of the island’s finest. The following day we pressed on to Mustique, a ritzy private isle that’s home to celebs like Mick Jagger and a yacht-friendly restaurant, Basil’s Bar. 

Our ultimate objective, though, was to reach the Tobago Cays, five tiny islets in the southernmost Grenadines where, Gangardine promised, we’d find secluded white-sand beaches, pristine snorkeling sites, and a marine sanctuary where we could swim alongside green turtles. “So where are the Cays?” asked my wife, Joy. With a keen hold of the helm, his response was simple: “Further.”

That search for adventure was exactly why we had come. It was our third Caribbean charter with the Moorings, which pairs families like mine with crewed yachts. Our first two trips were in the British Virgin Islands, where line-of-sight sailing, protected anchorages, and calm seas make the destination well suited for beginners. But with our sons aged 10 and 12, my wife and I wanted to push the limits and do some true open-ocean sailing, and this eight-day trip in the Grenadines was the logical next step.

After spending the night in Mustique’s Brittania Bay, we awoke to rainbows, plural, and the smells of fresh brewed coffee, warming croissants, and sizzling bacon — thanks to our chef, Magdalena St. Croix, a 63-year-old St. Lucian grandmother who has worked on yachts for decades. Immediately after breakfast, we set sail for Canouan, a three-square-mile island where Gangardine promised to plunk us into his favorite cove for snorkeling. He’d then drop us at Soho Beach House Canouan, a chic resort where we had a seafood lunch: conch fritters, prawn dumplings, mahi-mahi with tapenade and fresh lime.

After lunch and once again under way, the captain set two fishing lines to trawl off the stern. Then, suddenly, the whirl of a fishing reel: “Fish on!” yelled my older son, Jackson. Sure enough, the captain reeled in a 20-pound tuna, which he expertly filleted, then sliced into sashimi that Chef Maddie served to us before dinner that night. 

“It’s all part of the adventure,” Gangardine said.

Like all the best captains, he was talented at underselling the high points, whether a surprise catch or a beloved anchorage. Take, for example, Salt Whistle Bay, a glorious cove on the island of Mayreau. Gangardine told us we’d be going to “a beach,” but this place felt like a textbook Caribbean paradise. Dotted with rum shacks and windblown coconut palms, it instantly became our new favorite spot.

That is until we finally reached the Tobago Cays. This group of small, uninhabited islands, protected from the sea by a healthy barrier reef, has globally significant mangrove systems and sea-turtle nesting sites. Naturally we tested the waters, which are now protected as a national marine park.

“Dad, look! A turtle!” exclaimed my younger son, Tyler. Floating over thick beds of seagrass off tiny Baradal Island, we spied green turtles flapping their fins and swimming gracefully. The experience came on the heels of a stunning snorkel at nearby Horseshoe Reef, which teemed with tropical fish and healthy coral. 

The four of us replayed the adventure that night over a lobster dinner at Big Mama’s BBQ, on the islet of Petit Bateau. With long stone grills under a wooden canopy and weathered picnic tables shaded by coconut palms, it’s as close as you can get to an actual restaurant in this part of the Grenadines. Aside from one other group of boaters, who were also digging their toes into the sand, we were the only visitors. “It’s like another world,” Joy said. I had to agree.

A version of this story first appeared in the December 2024/January 2025 issue of Travel + Leisure under the headline “Adventure Awaits.”