Sailing the British Virgin Islands

Luxury Vacations: He arrived looking ready for island life however underneath his wrinkle-free surf trunks and faded Abercrombie & Fitch t-shirt was the presence of a man who had not a minute to spare, a man whose Blackberry and briefcase were as much an appendage as his arm or leg. My big brother Barry — senior partner in a New Jersey based law firm, single father and county coach for junior boys soccer — had left New Jersey for his first real vacation in six years.

My proposed remedy for his suburban stress was the somewhat unoriginal recipe of a Caribbean island, gorgeous weather, a seaworthy vessel, and copious amounts of rum. His unexpected response after six years of rewarding lock-down, was, "I'm in!"

After arriving at the Moorings marina in Road Town, the capitol of Tortola, home to our sleek 55-foot monohull, we were introduced to our captain and chef, Australian couple Tom and Jaquie. But shortly after we toured our elegantly appointed cabins, Barry started with queries of cell phone availability and Internet service. Mildly discouraged, I still had faith that the sun, the sand, the cool island breeze and life, in general, on our new floating villa would soon dismantle his daily worries of life back home.

Our seven-day voyage began on the island of Tortola, the largest of the 60 islands that comprise the British Virgin Island chain. Located in the northern Caribbean, Tortola is chock-a-block with soft, white sandy beaches and lush mountains. It also has a protected harbor strewn with a multitude of yachts in all shapes and sizes.

Our first visit was the Bright at Norman Island, just seven nautical miles south of Tortola. Helping to form the Southern perimeter of the Francis Drake Channel, Norman Island is often referred to as Treasure Island because of the vast number of pirates that once claimed these waters. One of its unique features is an area called The Caves, rumored to be the inspiration for Robert Louis Stevenson's book Treasure Island. Now if the beauty of the British Virgin Islands isn't enough to loosen the knots of suburban life, I'm not sure what is.

However with the balmy breeze offering a most refreshing relief to the beating sun, Jaquie's uncanny timing as she delivered a cold rum and Ting with some of our favorite bites, I could see Barry beginning to unravel. We launched ourselves overboard into a turquoise sea, swimming and snorkeling in and around the rock formations called the Indians, easily imagining what glorious treasures might have been sunken in the depths beneath our treading toes. Just below was the Rhone, a British steamer, which sank in 1867 during a hurricane and is now considered to be one of the very best wreck dives in all of the Caribbean.

We made our next stop at a floating bar/restaurant called the Willie-T. Yeah, this one's hard to describe without sounding shameless and irresponsible. Take yourself back, if you will, to your junior year of college. You've been drinking, life's pretty good, and no dare seems unreasonable. Got it? Now stick this local, anything goes-watering hole on a boat in the middle of the Caribbean and there you have it - the Willie-T. This I knew, of all things, would peak my brother's interest. You see the Willie-T has only one way to obtain the bar's famed t-shirt, and no, not with your credit card. You have to earn it by taking a topless dive off the top deck and strolling back across to collect your clothes. He may be a lawyer but he's still a guy and lucky for him there were some eager takers.

Sailing approximately 11 nautical miles from Norman Island, we reached Jost Van Dyke, a small and picturesque harbor protected by 1000 foot peaks, and home to the world famous Foxy's beach restaurant and bar. As fate would have it, Foxy himself was "in the house" as we anchored for a visit. It was an open-air, picnic table meets cabaret type party. We sat next to strangers, ate freshly caught Mahi Mahi, drank rum-inspired cocktails and shopped shamelessly at Foxy's beach-side boutique. 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 and celebrated life and the glorious sense of freedom before falling into hammocks hitched to coconut palms that lined the beach.

It was now and new and glorious morning filled with exceptionally blue skies. It must have been 11 a.m. when my brother surfaced from his mahogany cocoon below, which was a telling sign that my plan was working. The day ahead was filled with adventures at sea. The Caribbean was like a giant, wet wonderland where we would kayak, windsurf, swim and snorkel. Barry kayaked over to a tiny island known as Sandy Spit, which couldn't have been more than a few acres from end to end. He carried with him only a book, a towel and suntan oil. Yes oil, not block or screen. This was an ongoing comedy routine throughout the trip. He wanted a tan - refusing to consider that he might benefit from starting off with a higher screen, allowing the sun to do its thing slowly and methodically but instead he chose SPF 8 oil on day one of our trip. At Sandy Spit, we were down to a mere SPF 4. Two hours later I found an electric red Barry snoring beneath a lone palm.

Considered to be one of the most beautiful anchorages in all of the BVI, our next stop was Cane Garden Bay. We whiled away the hours, frolicking in the sea before happy hour at Myettes, a lively hotel, restaurant and bar. Starting off slow, the bar had just a few guests, and we could see that there was a wedding taking place down by the water. A band arrived, sort of Jimmy Buffet meets Bob Marley meets Motown kind of thing. I vaguely remember a rum-tasting session, becoming the official tambourine player for the band, and Barry, now two sheets to the wind, on the microphone with our Jimmy Buffet look-alike, singing his own special version of Mustang Sally. It was official. He was de-stressed. The eventful happy hour was followed by a feast of fresh crab and lobster, then a dinghy ride back to our bobbing home under the stars.

Our mornings were refreshing and lucid. Next stop: Marina Cay, located near Guana Island. This cay is roughly 10 nautical miles from Cane Garden Bay and is a picture postcard island, just minutes from Trellis Bay and the airport, making it a wonderful pit-stop for island shopping at Pussers company store, refueling, or buying a drink and taking in the sunset. We opted to grab a bite at Monkey Point then carry on to Virgin Gorda, which gets its name from its shape. Columbus described the island as resembling a plump woman with her belly in the air. There, our journey called notice to the luxury resorts of Little Dix Bay with its incredible spa and Biras Creek, an elegant bungalow style resort; the Bitter End Yacht Club, which offers a wonderful sailing school; and Baraka Point Villa, which comes with its own chef and crew.

Our last stops before heading back to Road Town were Cooper Island and the private island resort of Peter Island, where we took a swim at Deadman's Bay. But it was the mysterious Baths at Spanish Town, back on Virgin Gorda, which melted away the last faded wrinkles of city stress. At the Baths, giant granite boulders strewn throughout the beach and along the water's edge create stunning grottos, caves, wading rock pools and trails that lead to magnificent 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, how well Barry's law firm might do based on Tortola.

As I dropped a very dark, funny red version of Barry at the airport, I noticed that he was also a much more relaxed, looser version. We joked about leaving empty handed with all the talk of buried treasure. But teary-eyed and full of laughter we both knew where to find the treasures in our lives, and he was heading home to his. See all luxury hotels in the Caribbean

Jule Guaglardi

A veteran of the luxury lifestyle media industry, Jule Guaglardi had dedicated 16 plus years to promoting luxury travel, gastronomy and style through a vast number of media outlets. Wearing nearly every hat from the bottom up, Jule has since partnered in a small collection of luxury travel, cuisine and style magazines and co produced two television programs. Her new company Nomad Product...(Read More)

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