Vagabonding Field Reports: Sailing in the British Virgin Islands, Caribbean

Willy T. Tattoos. Me on the left and the girls.


Cost/day: $200

Chartering a boat isn’t cheap. If you are lucky and know the right people you could however, get a job as crew, stewarding, cooking or being a deck hand if you don’t have sailing qualifications. If you are not working then watch out for hidden costs such as moorings, docking, water and tips for the crew which may not be included in the bill.


What’s the strangest thing you’ve seen lately?

There is an excellent musician in St.Croix, U.S. Virgin Islands, called Kurt Schindler, he has a catamaran style boat which he uses as a stage. He parks it a few meters off the beach in Cruz Bay, St. John or off White Bay, Jost van Dyke and plays his gigs from there. I saw this rickety contraption with only an outboard motor, no sails and with banners flying in the wind, making it’s way considerable distances between islands.

Describe a typical day:

Morning: Wake up to the rocking motion of the sea. Leave the luxury of the air-conditioned cabin and go on deck, take in the white sandy beach and startling blue sea at White Bay, British Virgin Islands, jump in and have a swim.

Make breakfast and sail around to Great Harbour to get some ice and mangos and to meet with a friend I made there two years ago. Talk to Foxy, sitting in his bar, famous around the world for his music and Wooden Boat Regatta. Walk along the beach, catch up with friends.

Aternoon: See three dolphin, including a mother and calf swim right under the boat while leaving Great Harbour. Sail to Norman Island and scuba dive around The Indians: A group of rocks jutting out of the water. After lunch in the bay, motor over to the caves and scuba dive. See the extraordinary beauty of colors and light under the water with fish silhouettes and turtles. Go and moor up near the famous bar Willy T’s.

Evening: Have dinner on the boat and watch the sun set, then head to Willy T’s. It’s famous for its body shots. They usually involve drunk girls having stick-on tattoos applied to their naked breasts or bums or lying on the bar and having whipped cream put on their breasts and licked off by various people and other variations on this naked/alcohol/fake tattoo theme. Girls used to be able to get a free T-Shirt by jumping off the top of the boat naked but they have stopped this now. Richard Branson’s son had a birthday party there, his dad having an island nearby.


Describe an interesting conversation you had with a local:

At the Full Moon party on Tortola in the Bomba Shack I met some ladies from New York who had sailed in on a super yacht. The woman who owned the yacht said “My husband let me come here as a treat with my girlfriends. We’re all menopausal.” The captain of the boat who happened to be teetotal told me “Yesterday they spent the day wearing leopard print.” I tried to imagine asking permission to do something from a spouse, whether it would be worth it for a gigantic silvery boat, and what it would do to the image I have of myself if I decided to start wearing leopard sprint spandex and orange plastic boots…On balance I find the life of broke vagabonder much better for my peace of mind. And liver.


What do you like about where you are? Dislike?

I love the beauty and the abundance of marine life you can find there. I am particularly lucky to have been able to sail to between these beautiful islands. One of my favourite trips since being in the Caribbean was an overnight sail between Union island in the Grenadines and Trinidad. I was left in charge, on watch, alone a few hours at a time and got to navigate by the stars and see the sun rise over Trinidad and Venezuela. Also there is nothing quite like dancing the night away to live music barefooted, on a beach.

I dislike the pollution which effects many of the Caribbean islands making the water in many bays harmful to people and wildlife. I dislike seeing the excessively rich getting drunk and naked in pubic against a backdrop of the excessively poor. Though it’s true that tourism is responsible for a lot of revenue and employment on the islands.

I also dislike the crime that comes with the poverty, as well as the drug problem many islands have.  Recently I was in a club in St.Croix and it was held up. A few rounds were fired and one man was shot, he survived, luckily. I was grabbed by the above mentioned musician, Kurt Schindler , and we ran out the back. Also recently, my back pack was stolen along with my camera when I was living on a catamaran in St.Lucia. (Apologies for the lack of photos) This along with a bout of dengue fever has made for interesting times.


Describe a challenge you faced:

Surviving dengue fever, armed robbery, theft, a couple blackmail attempts, drug dealers and being marooned on St.Lucia for nearly six weeks when a boat I was to sail the Atlantic on broke down.


What new lesson did you learn?

It’s a challenge travelling when you don’t have much or in my case often no money. It can lead to some intense expieriences both good and bad. I have learned that in order to protect myself while traveling on the edge of experience to:

Love many, trust few, and paddle your own canoe.


Where next?

Plans are fluid at the moment but may include canoeing up the Amazon, prospecting for gold in Guyana and riding a motorbike around Bolivia.

If you would like to read some of my travel stories this is my blog: The Absurd Traveler’s Guide.


Until next time,



Posted by | Comments Off on Vagabonding Field Reports: Sailing in the British Virgin Islands, Caribbean  | July 7, 2012
Category: Adventure Travel, Backpacking, Female Travelers, Solo Travel, Vagabonding Field Reports

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