Sailing the Grenadines: Navigating the Caribbean’s Finest Passage

By six in the morning the southeast trades are already blowing twenty knots across the Bequia Channel, and Captain Rawlston “Rollins” Ollivierre has the mainsail half up before the anchor clears the water. He works without speaking, with the specific economy of someone who has made this passage hundreds of times and knows what the sky is telling him. The sky is telling him: move. By seven the sloop Esperanza is heeled fifteen degrees to starboard, spray lifting off her bow, the village of Port Elizabeth already diminishing behind the headland.

The Grenadines—a 90-kilometer arc of islands, cays, and reefs stretching between St. Vincent and Grenada—are commonly called the finest sailing waters in the Caribbean, which may be a function of marketing but is also, on mornings like this one, simply true. The trade winds are reliable. The channels between islands are deep and mostly obstacle-free. The cays offer anchorages of startling beauty. And unlike the more developed sailing grounds of the British Virgins, the Grenadines still possess stretches of water where the only other vessel in sight is a local fishing pirogue.

Rollins is 61, a Bequia man whose family has been building and sailing wooden vessels for five generations. His grandfather built whaling boats for the last active humpback whale hunt in the Western Hemisphere—a cultural fishery that continues on Bequia under a small IWC quota, deeply controversial but fiercely defended by islanders as an ancestral right. Rollins himself has never hunted. But he grew up with the boats: the lines, the joinery, the particular way a wooden hull talks to you through your feet and hands in ways that fiberglass does not.

Esperanza is 42 feet, built in 1979 from St. Vincent cedar and pitch pine, with a transom stern and a canoe bow that Rollins regards as the most elegant shape ever developed for a sailing vessel. She is not fast by modern standards—her best point of sail in these conditions is perhaps seven knots—but she is extraordinarily seaworthy, and watching her work through the chop of the channel is a lesson in design that has been refined over generations of open-sea necessity.

The passage south unfolds across the morning: Mustique at ten o’clock, its high green hills and the villas of the northern shore visible briefly through a squall line before it closes in; then the squall itself, fifteen minutes of hard rain and twenty-five-knot gusts that Rollins takes without adjusting the sails, the boat heeled hard and hissing through the water; then Canouan, where the anchorage at Charlestown Bay offers a brief respite from the channel chop. Rollins anchors off the town for thirty minutes, long enough for a cold drink at a waterfront rum shop whose owner has known him for thirty years.

The conversation at the rum shop is island-to-island news: who is building, who has sold, what the fishing has been like. The owner’s son has recently returned from studying marine biology in Barbados and is setting up a turtle monitoring program on Canouan’s Atlantic shore. Rollins listens with genuine interest. He has watched the hawksbill population around the Grenadines diminish over his lifetime, though he believes it is beginning to recover. He is not an environmentalist in any formal sense; he is a man who has spent sixty years paying attention to a specific body of water.

The Tobago Cays arrive in the mid-afternoon, when the light is beginning to soften and the water has shifted from blue to a layered sequence of aquamarine, green, and white over the shallow sandbars. The Horseshoe Reef, a partially submerged barrier that defines the anchorage, is alive with sea turtles—hawksbills feeding on the turtle grass beds that cover the sandy bottom. Rollins anchors in seven meters of water and swings the boarding ladder over the stern without comment. The implication is clear.

The snorkeling is extraordinary in the way that things are extraordinary when no superlative seems sufficient: ten, twelve, fifteen hawksbills moving through the grass beds with the unhurried elegance of creatures that have been making this particular circuit for fifty million years. The water is warm enough to be painless and clear enough to see the anchor chain on the bottom. Above water, the Esperanza swings gently at anchor, her cedar hull glowing amber in the late light, and beyond her the uninhabited silhouettes of Petit Rameau and Petit Bateau rise against a sky that is beginning to consider the colors of evening.

Dinner is flying fish—caught that morning on a trolling line Rollins streamed through the Bequia Channel—fried in a cast iron pan with garlic and island thyme, served with rice cooked in coconut milk and a salad of provisions from the Kingstown market. Rollins eats in the cockpit, watching the anchorage fill with other boats arriving for the night: a French catamaran, two American sloops, a German monohull. The Grenadines are not undiscovered. But Esperanza’s corner of the anchorage, chosen with the spatial reasoning of someone who knows exactly how she will swing at anchor through the night, is quiet.

In the morning there will be Union Island, and then the channel crossing to Carriacou, and eventually Grenada’s southern shore. But for now the stars over the Tobago Cays are extraordinary—the Milky Way legible in a way that no land-bound location permits—and the sound of the sea on Horseshoe Reef is constant and clean. Rollins goes below at nine. The boat moves gently. The turtles are still feeding in the grass.

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