He landed dressed for island life. But underneath his wrinkle-free surf trunks and faded Abercrombie & Fitch T-shirt was a man who had not a minute a spare, whose Blackberry and briefcase were as much an appendage as his arm or leg. My brother Barry—senior partner in a law firm, single father and junior soccer coach—had left New York City for his first real vacation in six years. My coercion tactics were simple: sailing and rum.
We arrived at our 55-foot monohull at the Moorings marina in Road Town, Tortola, the largest of the 60 British Virgin Islands. Entrusting ourselves to our Captain and Chef, Australian couple Tom and Jacquie, our seven-day voyage began.
Our first visit was the Bight at Norman Island, just seven nautical miles south of Tortola. Norman Island is nicknamed “Treasure Island” because of the pirates that once commanded these waters. One of its unique features is The Caves, rumoured to be the inspiration for Robert Louis Stevenson’s book Treasure Island. We snorkelled in and around the rock formations called The Indians. Below our treading feet slept the Rhone, a British steamer which sank in 1867 and is considered one of the best wreck dives in the Caribbean.
Next, we pulled up at a floating bar & restaurant called the Willie-T. Anyone courageous enough to topless dive off the boat followed by a shameless stroll back across deck was endowed with a free T shirt. Lucky for my brother, there were a few takers.
Approximately 11 nautical miles from Norman Island is Jost Van Dyke, a small harbour protected by 1000-foot peaks home to the world famous Foxy’s beach restaurant and bar. It was an open-air, picnic-table-meets-cabaret-type party. Before we knew it, the magic hour began to fall upon us, and Foxy, with guitar in hand, lit up the night. We danced in our bare feet before falling into hammocks hitched to palm trees.
Next up: Cane Garden Bay, one of the most beautiful anchorages in the BVI. We dropped by Myettes for happy hour. A Jimmy-Buffet-meets-Bob-Marley-meets-Motown band played. I vaguely remember a rum-tasting session, becoming the official tambourine player for the band, and Barry, who was two sheets to the wind, singing on the mic at the top of his lungs. This eventful happy hour was followed by a feast of crab and lobster and a dinghy ride back to our bobbing home under the stars.
Roughly 10 nautical miles from Cane Garden Bay was a postcard island Marina Cay, near Guana Island. This cay is minutes from Trellis Bay and the airport, making it a wonderful pit-stop for island shopping at Pusser’s Company store, refuelling, or buying a drink and taking in a sunset. We opted to grab a bite at Monkey Point, then carry on to Virgin Gorda, which gets its name from its uncanny resemblance to a plump woman with her belly in the air.
There, our adventure called notice to the luxury retreats of Little Dix Bay and Biras Creek, the Bitter End Yacht Club, which offers a sailing school, and Baraka Point villa which comes with its own chef and crew.
Despite all these magical moments, it was the mysterious Baths at Spanish Town, back on Virgin Gorda that melted away the last of Barry’s city stress. At the Baths, giant granite boulders strewn throughout the beach and along the water’s edge create grottos, caves, wading rock pools and trails that lead to pristine beaches. Believed to have been a spiritual and physical cleansing place for the Amerindians, the Baths remain a calming place that calls for meditation.
On our way back to the boat, we discovered the Mad Dog bar. We ordered their famous frozen pina coladas and pondered the meaning of life, love—and with a chuckle, the possible relocation of Barry’s law firm to Tortola.
As I dropped a very dark, funny red version of Barry at the airport, I noticed he was also much more relaxed. We joked about leaving empty-handed, having failed at finding buried treasure. But I think we had both discovered where to find the treasures in our own lives.