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HomeCaribbeanBeyond Trade Winds and Beautiful Scenery: How Caribbean Yacht Racing is Evolving

Beyond Trade Winds and Beautiful Scenery: How Caribbean Yacht Racing is Evolving

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Global yacht racing has changed dramatically over the last century-plus. In 1851, it was a 100-foot schooner that won the America’s Cup, while in 2021, it was New Zealand’s AC foiling monohull that did the trick. Sailing debuted in the 1900 Olympic Games, where there were six classes separated by size, from ½-ton to 20-plus tons. In 2024, we’ll see men’s and women’s formula kite classes added. Women could always compete in the Olympics, with men, but in 1988 women got their own classes. In the Caribbean, early sailboat racing was started by fishermen. The first back to shore met the biggest crowd of buyers and got better prices for their catch. It was five trading schooners that first faced off in a race around Barbados in 1936 in the Mt Gay Regatta. The Round Barbados Race is now a highlight of Barbados Sailing Week. Tourism, and the advent of fiberglass boats, brought recreational sailing and racing to the region in a bigger way. Antigua Sailing Week started in 1968, the BVI Spring Regatta in 1973, the St. Thomas International Regatta in 1974, and the St. Maarten Heineken Regatta in 1980. Today, warm weather and wind remain a big draw to Caribbean regattas. But that’s not all. The region’s regatta organizers are taking major trends in global yacht racing and making them their own in ever-changing and competitive formats. This creates a double draw for sailors to island start lines, especially in the winter and spring.

“The sailing conditions are spectacular with the trade winds, but Caribbean regattas are very well run and managed,” says Michele Korteweg, president of the Caribbean Sailing Association (CSA) and director of the St. Maarten Heineken Regatta. “Knowing that race management is handled professionally is a big pull for boat owners and sailors. Furthermore, the diversity in classes makes the regattas ideal for any type of sailor, pro or leisure. These include bareboat classes for chartered boats, and Island Time or Club Classes for liveaboards, smaller boats, and boats with limited crew, with fewer challenges to enter the racing and shorter/fewer races. It’s a great way for non-pros to participate in the regattas. Of course, we still see the Maxi’s with pro crews and similar boats that come to the Caribbean for serious competition. Add to this the welcoming nature of the islands and there’s really no reason not to participate.”

It’s also easy to do more than one regatta as the CSA has worked with organizers to create a calendar where regatta dates don’t overlap.

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Grenada Sailing Week. Credit Arthur Daniel
Grenada Sailing Week. Credit Arthur Daniel

Women in Caribbean Racing

Like the Olympics, women have always participated in Caribbean Regattas. Now, with a greater spotlight on this demographic by World Sailing, more events are embracing women’s participation on land and sea.

“Women are integral to race management in the Caribbean.
At Antigua Sailing Week (ASW), and in nearly every other event, women run the regattas, participate on race committees, and play leading roles in on-the-water management,” says Rana Jamila-Lewis, event manager. 

All-women teams are racing on the water too. Recent examples are Team Fope in the Caribbean Multihull Challenge and Chloe Need and her all-female crew who will be racing aboard the Salona 44, Moonflower 3, in Grenada Sailing Week, St. Maarten Heineken Regatta, BVI Spring Regatta, Les Voiles de St Barths and Antigua Sailing Week.

Local Flavor at the St Maarten Heineken Regatta. Credit Souleyman
Local Flavor at the St Maarten Heineken Regatta. Credit Souleyman

Distance & Round the Rocks Racing

Increased interest for offshore races continues globally with the Vendee Globe, Fastnet, and the Ocean Race, says the Korteweg. “We see this regionally with increasing interest in the RORC Caribbean 600.”

Course-wise, Caribbean regattas are moving back to round-the-island rather than round-the-buoy races.

“Marks are the gorgeous topography of the islands, cays, and rocks. This enables courses to be set with very clear easily identified marks but marks that challenge the course, having their natural wind shadows, changes in depth, currents, etc. It provides variability which is lost on courses only defined by laid marks/buoys,” says Cayley Smit, director of the BVI Spring Regatta.

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Race charter yacht at the St Maarten Heineken Regatta. ©LaurensMorel
Race charter yacht at the
St Maarten Heineken Regatta. ©LaurensMorel

One-Design & Diversity

There’s a continued adjustment of classes, says Alison Sly-Adams, president of ASW and past CSA president. “We’re seeing one-design fleets like the Diam 24s, IC24s, RS Elites, and Dragons fully chartered.”

Sly-Adams adds, “We encourage people to Rock up and Race. A broad range of boats from dragons to sport boats, race charters, and bareboats are available and mean that you literally can just fly in, enjoy a couple of practice days and you are ready to race.”

After Racing Regatta Village. Courtesy BVI Spring Regatta
After Racing Regatta Village. Courtesy BVI Spring Regatta

Multihulls Multiplying

The biggest changes Carol Gorvett, regatta manager for Grenada Sailing Week, and her team have seen is the number of multihulls that want to race. “In 2019 there were none registered. In 2022 there were 2. In 2023, we had a big jump to 6 and we expect the trend to continue.”

ASW is looking at introducing a multihull cruising class to accommodate the interests of the many cruisers in the region, says Jamila-Lewis. For scoring, “this will be run using the simplified system we apply to Club Class.”

Multihulls and foiling technologies gaining momentum is exciting because it not only pushes the boundaries of speed and excitement, but it allows large boats to make the trips within the islands much quicker than the standard journey, says Taro Singh, marketing coordinator for Barbados Sailing Week. “That means more opportunity for world-class racing within the region since travel time is cut down.”

Barbados Sailing Week. Courtesy Barbados Sailing Week
Barbados Sailing Week. Courtesy Barbados Sailing Week

Foiling Faster

There’s now a dedicated foiling event in the Caribbean, the Caribbean Foiling Championships (CFC) each December in St. Martin. Some events, like ASW, have added a foiling feature as this is a growing aspect of the sport.”

“In collaboration with the CFC, we are integrating a wing foil series at the start of our week. This 3-day race will be the 2nd year of the Antigua Foiling Championship. We expect a regional contingent of foilers to join us to race which brings additional energy as we kick off the week of keelboat racing at ASW,” says Jamila-Lewis.

Aerial View of Racing. Courtesy BVI Spring Regatta
Aerial View of Racing. Courtesy BVI Spring Regatta


“We are also proud to welcome Maxi’s back for this season, as the majority stayed in the Med in 2023 for maintenance,” says the CSA’s Korteweg. “We should be seeing a good solid number in the Caribbean. Leopard is back to defend some wins, but also newcomers like Galateia will be represented in the Maxi fleet.”

The St. Barths Bucket continues to be very popular with superyacht owners, guests, permanent crew, and professional sailors, says Jeanne Kleene, event manager. “At the Bucket one will see new builds and classic yachts. Of note is that within recent years, the Bucket began offering a ‘Corinthian Spirit’ class that has proven very popular. Innovations include a 90-foot class and a 100-foot class. There is also the option for social/non-racing entries whereby both motor and sailing yachts can participate in all social activities and enjoy dockage and preferred positioning for racecourse observation.”

Looking Forward to the 2024 Caribbean Regatta Season

“Regionally we seem to have been ahead of Europe and USA. We still see declining numbers at big multiclass regattas in Europe and the USA, but we are expecting an increase in participation in the Caribbean. Shipping rates are better, and people are far more comfortable traveling,” Korteweg says. 

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Carol M. Bareuther, RD, is a St. Thomas, U.S. Virgin Islands based marine writer and registered dietitian.

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