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By Amy Lynne Hayes
March 14, 2016
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Playing Pirate in the Caribbean
Amy Lynne Hayes recounts her adventures sailing the high seas of Anguilla on a a classic wooden 50’ gaff rigged West Indian sloop.

Playing pirate is no easy feat. To start, you need you need to be able to handle your rum. And by handle I mean not spill a drop on deck as you splash through the waves, swaying back and forth. It’s considered poor form, and bad luck according to sailor lore.



Secondly, and perhaps more obviously, you need a ship. These are somewhat harder to come by than the local liquid courage. But you need look no further than Sandy Ground in Anguilla, and Tradition Sailing. Tradition is a classic wooden 50’ gaff rigged West Indian sloop, built in 1978 on the Caribbean island of Carriacou. She’s a true classic in that she has neither winches nor windlasses, which means she requires plenty of man (or woman) power in order to operate.


We set sail on a summer evening, headed towards a spot called Little Bay. Captain Laurie Gumbs and First Mate Deborah Vos manned the sails while we kicked back and got in a few practice rounds for the sunset champagne toast. 



Even if you’re an avid sailor used to yachts, there’s something extra special about watching a crew sail without the aid of modern technologies. It’s more pure, almost… like a throwback to simpler times. You can’t help but feel the stresses of our fast-paced, digitally driven world melt away with each tack and jibe. Modern sailing is exhilarating, but the connection to time and place through a traditional vessel is a feeling that can’t be beat.


We arrived at Little Bay just before the sun set, allowing us time for a dip in the sea before a gourmet tapas dinner. The food is prepared fresh on shore earlier that day by Deb, and then assembled onboard. Pair that with the Caribbean version of moonshine and the transformation to official (luxury) pirate status is complete!



The beverages flowed and the laughter grew louder by the time the sun fully sank below the horizon. Lights were strung up above deck, creating an ambiance mirrored in the water. As several members of our group gave into the urge for a nighttime swim, we noticed the sparkle of bioluminescence, like Mother Nature’s version of champagne bubbles floating to the surface.



The sail back was undoubtedly more lively than the way out, the night air punctuated with our sung-at-the-top-of-our-lungs versions of 90s pop songs and karaoke classics. We capped off the evening with more song and dance at The Pumphouse, a wonderfully local bar on the banks of The Road Salt Pond. It’s a side of the island far removed from the manicured luxury resorts, but no less charming for its authentic local charm. If you ever make it there, be sure to seek out Laurie and Deb. And do tell them that I said hello.