Billowing sails and pirate tales

Luxury sailing in the Caribbean

Words & Photography Robin Esrock

Affluent residents of St. Barts are accustomed to welcoming mega yachts of the rich and famous. Unless you happen to know a billionaire, it’s highly unlikely you’d ever get close to one of these vessels, much less find yourself on the most beautiful boat in the bay.

It’s a topic that comes up repeatedly among the passengers of the SPV Star Flyer, a striking, 16-sail clipper with four towering masts, polished teak trims and enormous white sails. Turning heads from the Mediterranean to the Caribbean, it looks like a pirate ship sailed through an eighteenth-century wormhole.

Sailing with the breeze in high comfort is on many a bucket list, especially romantics with a pinch of salt in their veins. When I first board the Star Flyer late afternoon in St. Maarten, it takes my breath away. One of three tall ships owned and operated by Sweden’s Star Clippers, my week-long itinerary in the Lesser Antilles promises an adventure both familiar and exotic.

Well-appointed rooms, friendly international staff and a fine buffet are common on most cruise ships. Sallying forth under sail, chasing pirate lore and dropping anchor at small island communities are not.

Born and raised in a landlocked city, salt runs in my blood like integrity in politics. I can’t tell a jib from a topsail, a schooner from a sloop or the spanker from the anchor. Regardless of one’s prior knowledge and appreciation for sailing, everyone goose-bumped when the crew hoisted the sails at sunset. With speakers booming an epic soundtrack of Vangelis’s Conquest of Paradise, the wind thrust us forward in search of rich Caribbean bounty.

The 166-passenger Star Flyer is 115 metres long with a 15-metre-wide beam, and it’s not even the biggest ship in the Star Clipper fleet. The 227-passenger, 42-sail Royal Clipper holds the Guinness World Record as the largest square rigger in service. Both ships rely on the breeze to do the heavy lifting, with low-emission gas used for internal power, port docking and maneuvering through idle doldrums.

Fortunately, the wind in the Caribbean from December to April is so reliable you can bank on it, hence, the trade winds. It’s the perfect time to make up the leeway, learn your sailing lingo and discover wild legends among the beaches and coconut trees.

Calling into Anguilla, St. Kitts, Virgin Gorda, Jost Van Dyke and St. Barts, I’m sailing into a domain of buried treasure, mythical pirates and sloop battles. Borrowing books from the ship’s library, I dive into the Golden Age of Piracy, when motley crews of men—and occasionally women—plundered trade and war ships, all the while swearing impressive oaths of loyalty, democracy and non-discrimination, welcoming all who could be useful, and evenly distributing the spoils. The intrigue of pirates has long hijacked our popular imagination, the Black Flag inspiring countless legends in the Caribbean, including that of a buried treasure hidden deep inside the coastal caves of the uninhabited Norman Island.

Here, the Star Flyer dropped anchor so passengers could snorkel into the same caves that inspired Robert Louis Stevenson’s Treasure Island. The more I read about Henry Morgan and Calico Jack, Anne Bonny and the infamous Blackbeard, the more I get swept up in the region’s history, and the thrill of sailing under wind.

Operating a tall ship is both an art and a skill. Experienced passengers on board constantly debate our Polish captain’s decisions, analyzing the different sails in use, and the impact of the prevailing winds. With 3,344 square metres of sail, utilizing all four masts could easily blow us halfway around the world. The captain tells me that he often sails up and down during the night, providing invaluable experience for his navigation and ship crew, and using just 15 per cent of the fuel typically needed for a ship of this size. Cruising anywhere in modern luxury is a decadent affair, but with its comparatively low carbon footprint, large passenger sailboats like the Star Flyer suggest a more viable and sustainable cruising alternative.

When we dock in St. Kitts, I see a lineup of massive cruise ships docked outside a duty-free shopping mall. It’s the only time our vastly different cruise experiences meet, and it feels like we’re visiting from a different planet.

Occasionally, the wind howls over 25 knots, creating large swells that rock and roll the ship, stabilizers be damned. Sometimes, I reach for the Gravol or need to retreat to my comfortable cabin on the Commodore Deck, watching sea water rinse my cabin window. More often, the sea is as calm as a mirror, but sailing will always be an adventure, especially for landlubbers lacking sea legs.

Seventy-three international staff and crew operate efficiently under any conditions, spotlessly cleaning our rooms and preparing fantastic meals, cocktails and evening entertainment. There’s pirate parties and trivia nights, disco dancing and interpretive talks. Daily activities include swimming and snorkelling, various water sports, an on-board spa and opportunities to explore the history and culture of different islands.

Tenders deposit us on quiet beaches that are home to some of the Caribbean’s legendary sailing bars, like Soper’s Hole on Tortola and the Soggy Dollar on Jost Van Dyke. My personal highlight is a visit to Virgin Gorda’s The Baths—a series of rock pools, beaches and cave swims in the turquoise water of your dreams. Being on a smaller vessel with a minimal footprint means we can visit and interact with beaches and communities beyond the reach of giant cruise ships. My dining mates, a couple from Toronto, are cruise veterans with dozens of voyages under their belt. Both agree the tall ship had exceeded their expectations, with just the right combination of adventure and comfort.

Embracing the warm sea breeze, I stretch my arms towards a pod of dolphins cresting a few metres beneath me. I’m lying on the netted bowsprit at the fore of the ship, my favourite spot on the Flyer to soak it all in. It’s a giant hammock, of sorts, meeting the sea breeze and ocean spray head-on. I often lie back on the thick net to admire the clouds, or zone out staring at the waves. That’s when the dolphins appeared, gliding playfully in front of the bow, providing another singular moment of joy in a week of many.

Admittedly, not all passengers have the nerve to hang out at the bowsprit, much less take up the ship’s offer to scale the mainmast. Securely kitted with a safety harness, I climbed the rope ladder to a viewing platform 18 metres above the sparkling water. It provides a priceless and occasionally knee-shaking, bird’s-eye view of the ship, sea, islands and sparkling horizon.

Although travelling alone, I quickly find my crew of fellow bowspritters and mast-climbers. Spanning six decades of age, I gathered with my group to enjoy fine cocktails, fun company and tall tales at the Tropical Bar. No matter what boat you sail in, it’s the people you meet who create the paradise you find.

Reliably gorgeous sunsets and epic sail-aways are greeted each evening with champagne, cocktails and quirky maritime toasts suggested in the daily program.

An unannounced wedding takes place on the sun deck one evening, and the entire ship celebrates. Small ships just have that kind of vibe.

Later, we’re invited to follow the cruise tradition of dressing in white to sail the warm breeze under the spotlight of a full moon. Naturally recalibrating my balance with one hand steadied on the ship, I’d found my sea legs at last.

Everything moves a little slower under sail. Although the internet is available at the bar, it is pricey and limited. Most passengers agree that screens can wait. Sailing on a tall ship is about reading and resting, conversations and stargazing, staring into the distance, and wondering why it took you so long.

When we anchored in St. Barts, it was a thrill to find ourselves on the most impressive ship in the harbour, and nobody needed a personal invitation from a billionaire either. Any way the wind blows, it’s reassuring to know we can all find our own swashbuckling sailing adventure.