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(2018 - Fall Issue)


If I’d only packed what I needed—really, really needed—for a week cruising the British Virgin Islands, I would have breezed through security with just my handbag.

Not a carry-on bag, mind you, but a handbag. One with the usual purse accoutrement—hairbrush, sunscreen, wallet, passport—and the clothing I’d need tossed into the empty corners. Because, as it turned out, all I really needed on-board Prodigious, the six-cabin catamaran that is the largest of The Moorings BVI charter fleet, was a book, bathing suit, sandals, cover up, shorts and T-shirts. Life could not be simpler.

I’ve been fascinated by sailing the Caribbean since I spent a high school summer doing grunt work at a marine biology station in the southeastern Caribbean Sea. We worked long days bobbing on a dive boat, snacking on white bread sandwiches and mapping the health of the coral reefs. I was hooked, and so a week on a crewed yacht seemed like the perfect “adult” fit for my marine obsession. This time around, just luxury—high thread count linens in private cabins, gourmet cuisine, on-board Wi-Fi, air conditioning and an itinerary so flexible that we started each day on a whim.


As it turns out, the British Virgin Islands (BVI) are the perfect fit for working with a highly changeable schedule. The close proximity of the islands lends itself to that flexibility in day-to-day planning. Sailors have long called the BVI, “the place on the way to everywhere,” a nod to the many sheltered harbours that were a welcome pause in the lengthy trade routes between Europe and South America. The first European to discover the islands was Christopher Columbus in 1493 on his second voyage to the New World.

Prodigious’ captain, Martin Street, has sailed the globe but when he arrived in BVI seven years ago he knew this was a place he wanted to anchor. “First and foremost, BVI is known as a sailing destination—there are dinghy docks everywhere, bars and restaurants catering to sailors. There are 60 islands in the BVI—here we can jump between islands so easily. We have line-of-sight sailing—there’s much less open water sailing.”

Most charter boats depart from Tortola, an island of steep hills and the main transportation hub of the BVI. In the years of colonization—by the Spanish, Dutch and English—smuggling, piracy and privateering were rampant. Situated right on the treasure route, it was a magnet for the likes of Blackbeard, Calico Jack and Edward England. The islands were predominately a plantation economy until the Emancipation Act of August 1, 1834, after which the freed slaves lived off the fruits of the land and sea. In the early 1900s the tourist trade began to boom, especially the charter sailing industry, which became the backbone of the islands.

“There are two sides to the Caribbean,” explained Martin, who—together with chef Katie and steward Kay—cater to guests’ desires. “There’s the beach bar side and then there’s the golden beaches, palm trees, snorkelling. What people choose varies.”

If you’re like me, and all about the snorkelling and palms, a bathing suit and cover up is just about all you’ll need to pack. Prodigious is well outfitted with stand-up paddleboard, snorkelling gear, inflatables and a small dinghy to get from mooring to dock. Chef Katie works magic from a closet-size galley, creating fresh healthy meals with local ingredients like mahi mahi, lobster, pineapple and coconut. Within a day we’d set a dining rhythm: hors d’oeuvres and frosty tropical drinks on the fly bridge, meals alfresco at a table on the back of the boat. More drinks post-dinner while flopped in beanbag chairs on the webbed bow.


Our plan was to do a semi-circle around Tortola, sailing to Jost Van Dyke first, then south to Norman Island (reputed to be the inspiration for Treasure Island) and then on to Virgin Gorda. The cluster of islands is the top of mountains and volcanoes poking out above navy and turquoise waters.

They say that Jost Van Dyke was named after Dutch privateer Joost Van Dyke. The hilly island is known for its bar scene and beach parties—a hit with the sailing crowd—but, with a year-round population of about 297, there are still more goats than people. Before the arrival of motorized craft, the villages here were renowned for building sailing vessels.

We dropped anchor at Great Harbour, a sheltered bay at the base of 300-metre peaks, and revved up the dinghy to head for White Bay with its beautiful stretch of sand beach. The bay is synonymous with the Soggy Dollar bar, so named for the soggy state of the dollar bills used to pay for drinks after swimming ashore from an anchored craft. One does not go to the Soggy Dollar without ordering a Painkiller, a mix of crushed ice, dark rum, cream of coconut, pineapple and orange juice. The fastest way to banish thoughts of Canadian ice and snow is to sit under a coconut palm, Painkiller in hand (although the yacht’s steward Kay whips up her own version that gives anything on land a run for its money).

Next morning, just a two-hour cruise away, we anchored at Norman Island, slipped on flippers and masks and snorkelled The Caves. Dinner outside gave us a perfect line on the sunset, where we overnighted in The Bight, a well-sheltered, deep harbour. In between snorkelling and sunset there was a little reading, some sunning, more swimming, a hike to overlooks above Pirates Bight and the occasional nap. Bedtime was the gentlest of rocking; a bassinet on the waves.

By breakfast the next morning Martin had us well underway to our final stop, The Baths National Park on Virgin Gorda. The shoreline park is known for its unique jumble of enormous granite boulders formed when volcanic lava was thrown sky high during an eruption millions of years ago.

We dropped anchor, hopped into the clear waters and swam to shore. There’s a pathway winding and looping through the pile of boulders, with shallow grottos for quick dips along the way and breathtaking views mixing the granite grey with the deep blue and aquamarine of the sea.

Another day of swim-dry-repeat. And another day when I didn’t miss my clothes closet back home.

Travel Planner

To book your perfect sailing vacationin the British Virgin Islands, visit moorings.com and bvitourism.com.

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