IE 11 is not supported. For an optimal experience visit our site on another browser.

My Caribbean dream

Sunlight and motion woke me early, and I scrambled up on deck of the Star Clipper. As four stripe-clad crewman pulled lines and trimmed sheets, the ship shifted beneath my feet, responding to the wind and waves.
Cruising the Caribbean aboard the Star Clipper.
Cruising the Caribbean aboard the Star Clipper.Courtesy Star Clippers
/ Source: Islands Magazine

Sunlight and motion woke me early, and I scrambled up on deck of the Star Clipper. As four stripe-clad crewman pulled lines and trimmed sheets, the ship shifted beneath my feet, responding to the wind and waves. The night before I’d fallen asleep snug in my cabin as we motored out of the port at Dutch St. Maarten. But now with 15 crisp white sails taut against the breeze, we were really sailing.

I come from a Navy family, and spent my youth sailing with my dad. The intimacy you forge with nature when navigating the wind is a feeling like no other, and one I hadn’t expected to find on a ship carrying 170 passengers. “Quite a beauty, isn’t she” asked someone next to me, and next thing I knew I was involved in a four-way debate over wind speed (turns out we had 30 knots of wind, which explained the heel). I’d forgotten the camaraderie that exists between sailors, and in that moment, with the early morning sun on my skin and my bare feet on the teak deck, I knew I’d chosen well. This week-long Caribbean cruise that would take me to smaller ports on islands that came into their prime during the 18th-century days of the sugar trade. Experiencing them by sail would offer the kind of glimpse back into those days that I could never get on a modern megaliner.

The Star Clipper tied up to a small pier at Cabrits, a secluded town on Dominica, situated on the opposite end of the island from the capital, Roseau, where other cruise ships dock. There I found a Caribbean village going about its daily routine as it has, I imagine, for centuries: ramshackle wooden houses painted in a Crayola-box hues, laughing schoolchildren in blue-plaid uniforms and a man leading a goat down the center of the main road, vainly attempting to avoid the potholes.

I experienced a similar simplicity on the island of Terre-de-Haut in Les Saintes, part of the six-island archipelago of Guadeloupe. After spending the day on a perfect curve of beach surrounded by French-speaking sunbathers, I strolled back through the main town of Le Bourg and took my seat at a nearly empty café. I sipped my icy cold beer and watched as people who had come for the day from Guadeloupe’s larger islands boarded the ferry. A few nearby shopkeepers closed up and headed home, leaving me to enjoy the sunset in peace.

Life onboard the Star Clipper was equally serene. Passengers spent most of their time topside, reading in chaises on the top deck or swapping travel tales over drinks at the open-air tropical bar. Each night after dinner, I’d go up to the top deck to take in the stars, brilliant against the black-velvet night sky. As I scoured the heavens for constellations, I felt connected to all the adventurers who had sailed these same waters before.

Clearly, our captain loved his job. Although he’d just taken over the helm of the Star Clipper a few weeks before, he’d been sailing tall ships for decades.  Throughout the week, he was a regular sight on the bridge, relishing the hands-on attention that sailing requires. The wind kept its brisk pace all week, averaging force 7 on the Beaufort scale, and we maintained a steady 10- to 12-degree heel. Passengers laughed as they momentarily lost footing and grabbed for a rail or were hit by a splash of water that tipped out of the low side of the pool. It was a lively ride.

A few days later, as we neared Antigua, the captain got the chance to test the ship’s limits when we crossed paths with Star Clipper’s sister ship, the 227-passenger Royal Clipper. We all gathered on deck to take in the show. The Royal appeared on the horizon under motor, as we were. She passes across our bow and then circled behind us and came parallel along our starboard side. As both captains called commands, the respective crews began unfurling sails, one by one, to the cheers of the passengers gathered on both decks. The sails billowed in the wind, and before we knew it, the race was on.

Caribbean way of life

Slideshow  20 photos

Caribbean way of life

From chic to rustic, expensive to affordable, tourists looking for some sun and sand can find what they're looking for in the Caribbean.

Faster we sped for 20 glorious minutes, the ships racing. As the captain edged our smaller ship slightly ahead, the opposing ship fired a cannon blast; we responded with a solid bellow of the horn and kept our pace. All too soon it was over, and we waved as the Royal fell off behind us, continuing along its own journey to its next port.

Our ship set course for Falmouth, just north of the English Harbour, a port on the south side of Antigua that was headquarters to Admiral Horatio Nelson’s British fleet during the late-18th century, when hundreds of tall ships would have filled the harbor. While I was looking forward to touring the Georgian remnants of Nelson’s Dockyard, I realized that what we had just experienced had brought us much closer to the past than any port of call ever could.

Each issue of explores the most beautiful island destinations in the world, from tropical island outposts to the sophisticated gems of the Mediterranean. Our top-rate photographers and writers discover the quiet beaches, boutique hotels, and unique cultural experiences that make island travel unique.