Travel

Tall ship sailing in the Caribbean: a sustainable alternative to mega cruises

Bucket List columnist Robin Esrock visits the British Virgin Islands in search of pirate lore, Caribbean sunsets and a greener future for cruising

  • May 08, 2025
  • 1,564 words
  • 7 minutes
The Star Flyer (right) and Royal Clipper. (Photo courtesy Star Clippers)
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Unless you know a billionaire, getting anywhere near the mega yachts that flock to the British Virgin Islands each spring is a long shot, let alone stepping aboard one. It’s a topic that comes up repeatedly among the passengers of the SPV Star Flyer, a striking, 16-sail clipper ship designed for speed rather than cargo. With its four towering masts, polished teak trims, and enormous white sails, the Star Flyer turns heads across the Caribbean. Sailing aboard it feels like slipping through a wormhole into the 19th century, emerging straight from the Golden Age of Sail.

View from the top of Star Flyer's mast. (Photo: Robin Esrock)
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As a romantic with a pinch of salt in my veins, boarding the Star Flyer in Sint Maarten took my breath away. One of three tall ships owned and operated by Sweden-based cruise company Star Clippers, my week-long itinerary in the Lesser Antilles promised a familiar and exotic adventure. Well-appointed rooms, friendly international staff and a fine buffet are standard on most cruise ships. Venturing forth under sail, chasing pirate lore, climbing masts and dropping anchor in small bays is not.

The 166-passenger Star Flyer is 115m long with a 15-metre-wide beam, and it’s not even the biggest ship in the Star Clipper fleet. Their 42-sail Royal Clipper holds the Guinness World Record as the largest square rigger in service. Both ships rely on billowing sails 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, which is why past navigators called them the trade winds. 

As a passenger, it feels like I’m partaking in rich seafaring history while getting a preview of conscious luxury travel in the future. The contrast between our elegant, wind-powered vessel and massive cruise liners is striking, not just in aesthetics, but in environmental impact. The Star Flyer’s captain explains that the ship uses just 15 per cent of the fuel compared to a similar-sized engine vessel, resulting in a dramatically reduced carbon footprint. Beyond emissions, a smaller passenger capacity means less waste, reduced water consumption and minimal disruption to coastal environments and communities.

En-suite cabins in the Star Flyer. (Photo courtesy Star Clippers)
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The Star Flyer at full sail in the Caribbean. (Photo courtesy Star Clippers)
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Calling into Anguilla, Saint Kitts, Virgin Gorda, Jost Van Dyke and Saint 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 plundered trade and war ships​ ​while swearing impressive oaths of loyalty, democracy, and non-discrimination. Welcoming all who could be helpful and evenly distributing the spoils, the intrigue of pirates has long hijacked ​our​popular ​imagination. The Black Flag inspired 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. 

The Star Flyer. (Photo courtesy Star Clippers)
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Born and raised in a landlocked city, I struggle to tell a jib from a top sail, a schooner from a sloop, or the spanker from the anchor. Regardless of one’s ​prior ​knowledge and appreciation for sailing, the alluring draw of the ocean gets under the skin when the crew hoists sail at sunset to the booming soundtrack of Vangelis’s Conquest of Paradise. Operating a tall ship is both an art and a skill. Experienced passengers onboard constantly debate our Polish captain’s decisions, ​analyzing the different sails in use and the impact of the prevailing winds. With 3344 square metres of sail, utilizing all four masts could blow us halfway around the world. The captain tells me he often sails up and down at night, providing valuable experience for his navigation and ship crew. I see a line-up of massive cruise ships parked outside a duty-free shopping mall when we dock in Saint Kitts. It’s the only time our vastly different cruise experiences meet, and it feels like we’re visiting from a different era.

Occasionally, the wind howls more than 25 knots, creating large swells that rock and roll the ship, stabilizers be damned. Sometimes, I reach for Gravol or need to retreat to my comfortable cabin on the Commodore Deck, watching seawater rinse my cabin window. Sailing will always be an adventure, especially for landlubbers like me. Daily activities include swimming and snorkelling, various watersports, an onboard 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 highlight is visiting The Baths on Virgin Gorda, a series of rock pools, beaches and cave swims in bright turquoise water of ​your ​dreams.​

The Baths at Virgin Gorda. (Photo: Robin Esrock)
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Our smaller ​vessel means we can visit and interact with beaches and communities beyond the reach of​ the giant ​cruise ships. My dining mates, a couple from Toronto, are cruise veterans with dozens of voyages under their belts. 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 Star Flyer, where I can literally soak it all in. It’s a giant hammock that meets the sea breeze and ocean spray head-on. Throughout the week, I lie back on the thick net to admire the clouds or zone out, staring at the waves. That’s when the dolphins appear, gliding playfully in front of the bow, providing another singular moment of magic in a week of many.

Admittedly, not all passengers have the nerve to hang out at the bowsprit, much less take up ​the offer to scale the mainmast. Secured with a safety harness, I climb the rope ladder to a viewing platform eighteen metres above the ​sparking ​water. It provides a priceless and occasionally knee-shaking birds-eye view of the ship,​ sea, islands​,​ and sparkling horizon. Travelling alone, I quickly find my crew of mast-climbers and bowspritters. Spanning six decades of age, we gather for drinks and tall tales at the Tropical Bar. No matter what boat you sail in, the people you meet create the paradise you find.

Climbing the mast. (Photo: Robin Esrock)
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Life on the netted bowsprit. (Photo: Robin Esrock)
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Reliably gorgeous sunsets​ and epic sailaways​ are greeted each evening with champagne, cocktails and quirky maritime toasts suggested in the daily program. “To our wives and girlfriends… may they never meet!” An unannounced wedding occurs on the sun deck and the entire ship celebrates. Small ships tend to 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.  

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, lazing on the bowsprit, and wondering how to make sailing a full-time pursuit. When we anchor ​off ritzy Saint Barts on the weekend of a mega-yacht festival, ​there’s no doubt we’re aboard the most handsome sailboat in the harbour. What’s more, nobody needed a personal invitation from a billionaire.

The library aboard the Star Flyer is a great place to catch up on pirate lore. (Photo courtesy Star Flyer)
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