The Caribbean Sailing Association (CSA) has announced its rally calendar for 2026, offering cruising sailors an array of organized events designed to explore the waters of the Caribbean alongside fellow adventurers. The new schedule promises a diverse mix of regattas, rallies, and special gatherings that celebrate the region’s rich sailing culture.
A notable highlight of the upcoming season is the inclusion of a stop in Dominica in February 2026, where participants can join the Salty Dawg Rendezvous.
“The rally concept is not new, with events such as the ARC (Atlantic Rally for Cruisers), Oyster Yachts and more latterly the Salty Dawg Association offering rallies to and from the Caribbean or from the Caribbean around the world for many years. The newest development is racing events incorporating rallies, the Caribbean Multihull Challenge is a great example, which has developed this format in the last few years along with organised gatherings of cruisers throughout the region and the season,” shared the CSA in its newsletter.
Antigua Sailing Week (ASW) is also undergoing a format transformation for 2026, shared the CSA in its newsletter. Organizers have announced a return to destination sailing around Antigua, combining both racing classes and a rally option tailored for cruisers.
The 2026 calendar also introduces feeder races such as the Rum to Spice from Barbados to Grenada and La Vuelta Culebra in Puerto Rico. These events serve as perfect preludes or follow-ups to larger regattas, fostering regional connectivity and camaraderie, said the write-up.
CSA President Bastien Pouthier expressed enthusiasm about the evolving calendar, stating, “From Barbados to Puerto Rico and many islands in between, we are delighted that our members are developing events that are more inclusive and bring sailors together for the simple joy of sailing.”
Organized by prominent entities like the World Cruising Club and the Salty Dawg Association, the calendar features a blend of regattas, rallies, and social gatherings. The rally concept, long popular in the cruising community, continues to evolve with events like the Caribbean Multihull Challenge, which has developed a dedicated rally class in recent years.
Manager of St. Maarten Yacht Club, Saskia Revelman, noted the significance of this development, saying, “Our rally class at the Caribbean Multihull Challenge is very popular, especially as it’s the only dedicated multihull regatta in the region. For December 2025, we’re adding a rally component to the Course D’Alliance, which will take sailors from St. Maarten to Anguilla and St. Barths.”
For more details and to view the full calendar, enthusiasts are encouraged to visit www.caribbean-sailing.com/rallies. The 2026 schedule promises an exciting year of sailing, fostering community, competition, and exploration across the Caribbean’s stunning islands.
Full calendar below:
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