
“Sailing Life is What I Choose,
Imported Rum is My Kind of Booze…
Sailing Life is Made For Me,
I Raise My Spinnaker and I’m Free…”
– Singer/Songwriter Eric Stone
The water is blue – many shades of blue, in fact – the wind is blowing but hardly howling, captain and crew are going “fast enough to get there but slow enough to see” as the Jimmy Buffett song possibly playing on the stereo says, and there’s plenty of rum on board.
It’s just another idillic day aboard a sailboat in the Virgin Islands.
This is more than an island paradise. It’s an island-hopping paradise. Wake up in Soper’s Hole – where Blackbeard used to hang out before making pirate raids – and go to sleep under the stars in Cane Garden Bay, a place Buffett so accurately portrayed in one of his original sailing songs, “Manana.”


In between, there is diving the chimneys, snorkeling the caves, wading through the Baths, diving off Willie T’s and killing pain with the Painkiller, the local drink served at spots like the Soggy Dollar Bar, where dollars are soggy because boats anchor in the harbor and crews swim to the beach.


This article is all about that sailing live, providing information and photos about sailing the Virgin Islands, and in particular the BVIs. While you may start in St. Thomas and spend time in St. John in the USVIs, it’s the BVIs where most of the scenery, activities, diving and particular the great beach bars are located.
Chartering A Sailboat

Boats are chartered from various locations throughout the Virgin Islands.
The primary port of departure is Tortola with its ample number of chartering companies. It is easy to stock the boats with provisions from here; order in advance and the bigger companies deliver right to the dock (the charter company can make the arrangements).
Additional daily provisions can be found at just about every harbor. And the bartering system with other boats is alive and well in the BVI.
Boat prices range from about $5,000-10,000, depending on the size and type of vessel and the length of the journey.
One recommended addition for any boat is a bartender. Bring your own, and if you are lucky, he/she will be a rum-loving fool like Luau Larry, who serves as “mixologist” on PubClub.com’s island adventures.
“Sailing Live is What I Choose, Imported Rum is My Kind of Booze”
Indeed!
Sailing the BVIs – The Islands & Must-To Destinations
“We hit the beach in Anegada
To catch our breath and catch some rays.
And watch the sunset on the water,
To end the perfect island day…”
– Eric Stone

The Baths on Virgin Gorda are the most beautiful place in the entire BVIs.
Then again, the most beautiful place could be the Bitter End Yacht Club elsewhere on Virgin Gorda.
The best daytime bar is the Soggy Dollar Bar on Jost Van Dyke. Then again it could be the Cow Wreck on Anegada.
Whichever way the skipper sets sail for in the BVIs is sure to bring smiles to the faces of the crew. What’s best, the close proximity of the islands to each other means it’s possible to do just about everything in a relatively short timeframe.
A week is enough to take it all in at a Caribbean pace, 10 days is probably the ideal sailing time and two weeks is dangerously close to contacting the Caribbean equivalent of what in Key West is known as “Keys Disease.”
There are many “must see, must do” locations in the BVIs. They include:

• The Baths, Virgin Gorda. Big rock formations sit along the shoreline adjacent to a gorgeous, soft-sand beach. Over time, the ocean has eroded the boulders to the point they form a Caribbean version of the Turkish baths, allowing for ankle-deep exploring. It’s an up-and-down, minimally-marked adventure. The rewards include Devil’s Beach, a near-private cove with water so clear it’s easy to see the angelfish swimming without a mask. The eventual destination is the Top of the Baths, a restaurant/bar with a view of all below.
• Bitter End Yacht Club, Virgin Gorda. A high-end resort, the Bitter End is a located in the beautiful – make that jaw-dropping gorgeous – northeastern part of the island. This is apparent from the moment of the approach (careful of the marked reef). Thatched huts peek out from the wooded hills and a sailor’s delight awaits – a dock with overnight docking! On shore, the Emporium Pub serves potent 16-ounce rum punches, mangroves by the pool area provide stunning views and a scenic and delicious meal awaits at adjacent Saba Rock.

• Sunsets and the Cow Wreck Bar, Anegada. The longest sail in the BVIs – about three hours – is worth it. Grab a mooring ball at Pomato Point, dingy ashore to the Anegada Reef Club and Hotel and catch a cab to the Cow Wreck. Anegada is as renowned for its lobster and the lobster salad sandwiches here are fantastic. So, too, is the setting: right on a white sand beach with windsurfers cutting up the ocean in the eye’s frame. Then, hustle back for sunset because, as Eric Stone sings, it’s an end to the perfect island day. Be careful of the “single-file” marked reef.
• The Caves and Willie T’s, Norman Island. A superb snorkeling spot, the Caves are a pair of entrances into the side of a cliff. Snorkelers are surrounded by colorful fish the moment they jump into the clear, aqua-blue water. Don’t be startled by the gigantic barracuda; he’s seen it all and is not interested in you. Do this in the late afternoon and then ’round the bend to Willie T’s, the anchored pirate ship where people gather at Happy Hour to drink like fish and jump off the railing into the water below. Often in the nude.
• The Soggy Dollar Bar and Foxy’s, Jost Van Dyke. The sun-spectacular Soggy Dollar Bar sits behind a glistening beach framed by palm trees and surrounded by an aqua-blue bay. It created the painkiller (served in souvenir plastic cups), drawing boats from throughout the Virgin Islands. And just down the beach, Gertrude’s makes the best (original?) bushwhacker in the islands. Around the corner, the legendary Foxy’s is, quite simply, a party.
• Sandy Spit, off Jost Van Dyke. A spit of an island, it’s a tiny piece of paradise ringed by a powder white-sand beach. Set the anchor and snorkle ashore. Sure, Sandy Spit can be circumnavigated in about a minute and the snorkeling is far from spectacular. But the place is ideal for swimming, sunning and enjoying the fact that you are here.
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