crow flies”, arguably have the most intense journey down to the Caribbean. There are essentially two options to get down from the east coast of America to the Caribbean by sail: The Thorny Path or the I-65. The Thorny Path is near-shore,
navigating from Florida through the Bahamas, flying by Turks and Caicos, skirting Puerto Rico and ultimately battling squally weather to beat around the Virgin Islands. The I-65 sounds simpler because it is: head east until you reach a longitude of 65 degrees west before turning south towards the Virgin Islands. There is no shame in entering the Caribbean racing circuit half way through the season. There is plenty of racing still to be had with the double-header in the Virgin Islands starting at St Thomas International Regatta, celebrating 50 years in 2024, followed by the BVI Spring Regatta early April. Nonetheless, American sailors
have made the annual journey south for the winter for decades and more are pushing further south with their racing machines. In the 2023 St Maarten Heineken Regatta, an entire class of 50-60 footers were from the USA, where top US teams Hooligan (TP52) and Privateer (Cookson 50) got to battle it out for the first time in the Caribbean arena. Not all teams are required to
make the journey under their own keel. Many owners choose to ship their vessels down to the Caribbean. Some do this to avoid the wear and tear of an ocean crossing, while others do so to manage a packed racing schedule. Cape 31 Flying Jenny raced in
Key West, Florida less than a month before the team kicked off their racing season in the Caribbean in March with the St Maarten Heineken Regatta, St Thomas International Regatta and BVI Spring Regatta.
60 SEAHORSE
Above: five Volvo 65s and two Volvo 70s on the start line at the Sint Maarten Heineken Regatta. The Caribbean season is a real treat for spectators. Right: one of many race- ready yachts available for charter, the J/122 El Ocaso is a past winner in St Maarten, St Thomas, BVI and Antigua
Then the boat went back into its container and over to the UK where the team continued to compete at a high level for their summer circuit. Port St Maarten, St Thomas and
Antigua are all accessible, international ports that shipping companies such as Sevenstar and Peters & May service to bring yachts to and from the US and Europe. Many who ship choose to begin and end their season in Antigua with the RORC Nelson’s Cup to start, Antigua Sailing Week to finish and a whole lot of islands, regattas and parties in between. For those sailing back home,
the Antigua Bermuda Ocean Race returns in 2024 as a competitive option for the return route. East Coast US and Canadian boats as well as European teams will all route back home via Bermuda, often right after Antigua Sailing Week ends the regatta season. So why not finish the Caribbean racing season with an ocean race?
Itinerary 4: CYOB - Charter Your Own Boat Nothing goes to windward quite like a 747! Plenty of sailors choose to fly
in and charter a local boat to get all of the best of the Caribbean with none of the hassle. The Caribbean Sailing Association
(CSA) and the member regattas offer great support and resources for first-time Caribbean sailors. You can explore a selection of reputable yacht charters on their respective websites and choose from race charters, bareboat, or individual berths. Race charters of 24ft trimarans, performance 40-footers, all the way up to professionally crewed Volvo Ocean Race boats and beyond are on offer through agents like LV Yachting. Bareboat charters are available from Sunsail and Dream Yacht Charter, and are in high demand for St Maarten, BVI and Antigua Sailing Week. Every regatta has its own offering, fleet and onshore amenities that can suit families, groups of friends or business colleagues. No matter the boat or crew size,
or your starting or end destination, the Caribbean Sailing Association’s packed event calendar should absolutely be included in your winter sailing itinerary.
www.caribbean-sailing.com
❑
LAURENS MOREL/ST MAARTEN HEINEKEN REGATTA
PAUL WYETH
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