Caribbean Sailing Association announces 2026 Rally calendar

Boats at anchor during the 2025 Caribbean Multihull Challenge © Caribbean Sailing Association

The Caribbean Sailing Association (CSA) is thrilled to unveil its new Rally Calendar for 2026, designed for cruising sailors eager to explore the vibrant waters of the Caribbean in the company of fellow adventurers.

The calendar features an exciting lineup of events tailored to unite sailors while enjoying organized cruising experiences. Highlights include renowned World Cruising Club events, engaging gatherings with the Salty Dawg Association, and an array of exhilarating regattas across the region that offer a dedicated rally class.

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.

Manager of St. Maarten Yacht Club Saskia Revelman says, "Our rally class at the Caribbean Mulithull challenge is a very popular format, especially as it's the only dedicated multihull regatta in the region and for our December 2025 regatta we are adding a rally class to the Course D'Alliance which takes sailors from St Maarten to Anguilla & St Barths."

Antigua Sailing Week (ASW) is also making changes to its format for 2026 which sees a return to destination sailing around Antigua and will offer both racing classes and a rally option perfect for cruisers. Organiser Alison Sly-Adams says, "With the separation of the racing classes into a new earlier racing event, (Antigua Racing Cup), it's created the opportunity for ASW to return to the original concept of the event which focussed on fun at a different location each evening. Crews can chose whether they want to enter the racing classes or simply cruise in company, enjoying a new piece of coastline daily. Once at the destination, everyone is together on the beach to enjoy classic Caribbean hospitality."

"Spanning from Barbados to Puerto Rico and many islands in between we are delighted that our members are developing events which are more inclusive and unite sailors for the simple joy of sailing." says CSA President Bastien Pouthier.

Joining the calendar are a also feeder race from Barbados to Grenada, aptly named Rum to Spice & La Vuelta Culebra in Puerto Rico.

Full calendar here

Caribbean Sailing Association announces 2026 Rally calendar - photo © Caribbean Sailing Association