Antigua, the “Land of 365 Beaches” is in the middle of the Leeward Islands of the Lesser Antilles, a few degrees north of the Equator. Its culture has been strongly influenced by the British Empire, of which the country was formerly a part. I visited the island in April of 2019 to observe the annual Antigua Sailing Week; a few days of competitive sailboat racing off the rugged southern coast, and a fabulous party atmosphere ashore.
The sound of a canon announced the opening of the Sailing Week, when vessels in all sizes from 23 nations around the world, compete in different classes for the overall prize, The Lord Nelson Trophy. In most cases, the outcome of a whole week’s racing is decided by seconds.
The most interesting to me part of the regatta is the competition amongst the 80 to 100 foot, single mast boats with large crews. Many boats sail across the Atlantic and/or Pacific Oceans to participate in the event, while other crews fly to Antigua, Guadeloupe or one of the nearby Caribbean islands, rent a bareboat and compete after shake-down sailings.
It’s been more than 55 years since I have sailed competitively, but once you get the sea in your veins, it’s very difficult not to get excited when a sailing competition is at hand.
In my youth, I had cut my teeth on Star keelboats and Flying Dutchman sailing dinghies; 3-person, 23 feet (Star) and 2-person 20 foot (Flying Dutchman), Marconi-sloop-rigged, extremely fast racers.
I was attracted to the Star keelboats by the very high speed the boat can achieve and the radical hiking position adopted by the crew and the helmsman, who use harnesses to hang off the windward side of the boat. The Flying Dutchman was even faster than the Star and the crew (i.e. me) had to hang by a trapeze harness fastened to the top of the mast with only my tippy-toes holding on to the gunwales. The Flying Dutchman made its Olympic debut at the 1960 Olympics Games and was removed as a competitor after the 1992 Games.
Antigua Sailing Week is one of the Caribbean’s most prestigious regattas with more than 100 boats participating each year in classes 0 to 8, plus a multihull class and 2 bareboat categories.
Watching the sailing boats compete is absolutely thrilling, especially when you are in a craft inside the middle of the course. This time I was an observer, not a competitor.
The Sailing Week is also a good excuse for a giant party ashore, where locals and visitors, including the competing crews, spend time getting to know each other, dancing and drinking — Veuve Clicquot was one of the sponsors and English Harbour Antigua Rum was another — and in general, socializing in a very relaxed atmosphere. Or, as the locals call it, “liming”.
Late spring is a great time to be in Antigua. The temperature is not high, usually in the 70s °F, the water is warm and the throngs of tourists that come once the school year has ended have not yet descended on the island. The residents are friendly and the food is exceptionally fresh and flavorful, especially the fish and seafood. And the rum, both as part of a cocktail – rum-punch or rum-and-coke or any of the concoctions local mixologist invent – or as a sipping spirit, is particularly enjoyable and invigorating.
I saw a number of the crews taking part in many of the parties, but most left early in the evening, so they would be clear-headed for racing the next day. A “drunken sailor early in the morning” might be a great idea for a 19th century sea shanty, but can be an accident-ready-to-happen in competitive racing, where skill and pin-point timing are essential.
Prior to the prize giving at Nelson’s Dockyard, the America’s Cup Trophy is displayed. “The Auld Mug” is the oldest international sporting trophy in the world, originally awarded in 1851 by the Royal Yacht Squadron for a race around the Isle of Wight. At the end of the week the Antigua Sailing Week comes to a conclusion with the Final Awards Ceremony and a spectacular After Party.
My sailing days are over. Yet, I could not resist the calling of the sea when I saw the multi-colored spinnakers while the vessels were racing with the wind. My heart skipped a beat!
The author received a complimentary cruise, but as always, we are dedicated to giving you unbiased accounts of our experiences. See our Disclosures page for more information.
Manos Angelakis was one of the founders, the former Managing Editor for 25 years, the former Managing Editor Emeritus, and former Senior Food & Wine Writer of LuxuryWeb Magazine. He passed away in 2025 as an accomplished travel writer, photographer, and food and wine critic based in Hackensack, New Jersey. As a travel writer, he wrote extensively about numerous cities and countries. Manos was also certified as a Tuscan Wine Master and traveled to wine-producing areas in order to evaluate firsthand the product of top-rated vineyards. His articles in other publications include Vision Times and Epoch Times.
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