From contraband to sunset cruises, Tradition Sailing

Sun, sea and sand… and, oh, not to forget, sail with Tradition Sailing!

Anguilla, an upmarket Caribbean destination, has been blessed with open waters that grant sea lovers with the felicitous opportunity to explore its breathtaking underwater world, whilst being left in awe by the surprisingly beautiful shoreline of the island.

From the days of migrating to other islands in order to find work, Anguillians, as resilient as they are, turned the connotation of sailing from “long voyages away from loved ones” into “an activity which soothes the soul”. Thus, sailing has been woven into the historical fabric of the island; and, this, indeed, makes it quite ironic to sail onboard ‘Tradition’!

Tradition Sailing Deluxe Sunset and Starlit Evening Sail

Look out yonder! What a beauty she is! Bobbing in sync with the waves! Nestled in the harbour surrounded by many marine vessels but she, Tradition, stands out with its mast and sleek red ‘body’. Close your eyes… Imagine experiencing some of Anguilla’s exquisite treasures… scrumptious tapas… the romantic atmosphere created when sailing out to the sunset and sailing underneath a chandelier of stars…  One word: Spellbinding!


All passengers for the semi-retired sloop, Tradition, gathered at the Sandy Ground jetty where the crew of three loaded the dinghy boat in preparation for the evening’s laughter and adventure – the ‘Deluxe Sunset and Starlit Evening Sail’. Give your feet a break and kick off your shoes! “… place your shoes carefully in the box to be returned upon arrival to the jetty” – sounds more like it! And with that, we were off!


Once settled, Deborah, affectionately known as Deb, poured us a glass of their famous cocktail – a mixture of passion fruit juice and Prosecco champagne – followed by a brief history about Tradition by Laurie, the owner and captain, which went like this:

Tradition was hand-crafted, in 1978, on the beach in Carriacou, Grenada. Tradition is a classic wooden 50’ gaff rigged West Indian sloop. Built for sail trading through the Caribbean, she worked the trade winds, carrying cargo – including contraband from St. Barthelemy where the smuggling trade in alcohol and cigarettes thrived as it was a tax-free haven until as recently as the 1990’s.

Instead of island trading, Tradition is now living in semi-retirement in Anguilla and now sails to capture the romance of a Caribbean past.”

After smooth sailing out from Sandy Ground Bay heading towards Little Bay, it was time to mingle with the crew and all the other passengers. It was very delightful to get to know more about those who would be sharing my first sailing experience with me….Picture Time!!!  All smiles for the camera!


Better yet! Tradition has a large, comfortable deck – a great chance to move around and take in the scenery from different angles but where walking barefoot on the deck is concerned, Balance is definitely key! Almost convinced that I only had ‘land feet’, after a couple more stumbles and practice, I finally learned how to engage my ‘sea legs’.


Join in the excitement and action! Whether you are interested in learning a bit about sailing; or wish to exhibit your sailing skills, the crew more than welcomes you to pitch in with the sail handling – adjusting the sails and/or be in control at the helm!

Tradition is equipped with a tiller and the captain will assure you that it is not as easy as it looks. Nevertheless, once your brain gets used to the fact that the boat turns the opposite direction to where you move the tiller, you’ll have steering ‘down packed’- the feeling of accomplishment is very satisfying.


As we sailed away, basking in the beauty of the array of colours emitting in the scenery, the sky was “most richly tinged with the changeful rose color, and purple, and gold of the sunset’s glorious hues, which shone forth in still greater lustre… It was a scene never to be forgotten.” Louisa Anne Meredith


Utilising the last rays of the soon-leaving sun, we were captivated by the geology of the landscape – the limestone cliff which nestled but presented the pelicans and birds up above – and the tranquility of the setting while dusk prepared us to be greeted by the dark, starry night.

The moon’s welcoming shine was an indicator that it was time for another anticipated pass time – dining! With the moon, stars and candlelight as our only source of light, we helped ourselves to the delectable tapas which were accompanied by champagne or any other available drink of our choice.

The journey back to Sandy Ground Bay was one of mixed emotions – sad to be leaving after a fun-filled and refreshing evening but grateful for the unforgettable experience as well as the opportunity to “embrace the magic of sailing at night that seafarers have loved for centuries”.

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