2026 Caribbean Regattas, Trophies & Rule Application Rundown

Happy New Year to All!

With many of you are around the world returning to work post holiday, we thought we’d send a splash of the Caribbean, to give you some New Year inspiration for things to do or dream about!

As the season is about to kick off, we wanted to let you know about all the amazing events and trophies we have lined up for you in the Caribbean this year. Check out details for applying for your CSA Ratings, information on Dual Scoring, a new CSA Travellers Trophy category, the Budget Marine Windies Multihull Trophy Year 2, The NEW Rally Calendar & the Dinghy Circuit as well as of course our International 5 Year Events Calendar.

CSA Rating Applications for 2026

The Caribbean Sailing Association (CSA) is excited to announce the opening of the application process for boat ratings ahead of the highly anticipated 2026 International Racing Season.

President Bastien Pouthier says’ ‘We encourage all boats planning to race in the Caribbean this season to apply for their ratings as early as possible to ensure a smooth and timely measurement process across the islands.’

To apply for your rating, please visit www.caribbean-sailing.com/apply-for-rating. The payment for ratings can also be completed online, making the process quick and convenient for all participants.

Dual Scoring for 2026

In October, the CSA announced is new appointment as the IRC Caribbean Rating Authority, If you missed the announcement,  here it is: https://caribbean-sailing.com/csa-joins-forces-with-irc-to-bring-dual-scoring-to-the-caribbean/

If you plan to head to the region and need an IRC rating, check out how to do this in the Caribbean here: www.caribbean-sailing.com/irc to begin the application process.

The 2026 International Racing Season will kick off with Barbados Sailing Week in January, marking an exciting start to the competitive sailing calendar. Six of the regattas have confirmed they are offering dual-scoring: Barbados Sailing Week, Grenada Sailing Week. St. Maarten Heineken Regatta, BVI Spring Regatta, St. Thomas International Regatta & the Antigua Racing Cup. Allowing boats to race under both systems makes the regattas more accessible and more globally relevant.

The International 5 Year Calendar & Notice of Race Quick Links.
Please review links to each regattas Notice of Race.
https://caribbean-sailing.com/caribbean-sailing-association-notice-of-race-summary-2026-season/

Check out the full calendar: https://caribbean-sailing.com/international-regatta-5-year-calendar/

And all Caribbean Events in Date order here: https://caribbean-sailing.com/calendar/ 

Travellers Trophy 2026 –  A New Race Charter Category

The CSA Traveller’s Trophy, awarded by the Caribbean Sailing Association (CSA), recognizes the most successful and traveled yacht across multiple Caribbean regattas. The trophy has been in place for more than 25 years. In 2026 there is a new category meaning two trophies awarded – private boats & new for this year charter boats.

Qualification includes racing in a minimum of three regattas, including one in an away region & one major event. It celebrates both excellence in performance and the effort of traveling between events

Check out full details: https://caribbean-sailing.com/csa-travellers-trophy/

The Budget Marine Windies Multihull Trophy

The trophy is designed to encourage offshore multihulls to participate in more Caribbean regattas and offshore passage events. The second year of the circuit kicks off at Barbados Sailing Week 2026.

The 2025 champions will be awarded at the Caribbean Mulithulll Challenge at the end of January in St. Maarten. The series, sponsored by Budget Marine is now open for 2026 and the CSA will score every mulithull class and regatta throughout the season to determine the 2026 champion.

Check out full details:  https://caribbean-sailing.com/csa-windies-multihull-trophy/

The NEW Rally Circuit

The Caribbean Sailing Association’s rally calendar features a variety of sailing rallies across the region, promoting adventure and camaraderie among participants while exploring the beautiful Caribbean waters.

https://caribbean-sailing.com/rallies/

Dinghy Regatta Circuit

If dinghy sailing is more your bag, a healthy regional dinghy sailing calendar is in place throughout the islands. While focused on youth events, a number of events include laser classes for all age groups and welcome guest sailors.

https://caribbean-sailing.com/dinghy/

We look forward to seeing you racing this coming regatta season. For any queries please emailnews@caribbean-sailing.com

About the CSA

The Caribbean Sailing Association (CSA) promotes and governs sailing in the region by administering a unique handicap rating rule for racing, organizing events like the Caribbean Dinghy Championships, and providing training and logistical support for members. A collective of yacht clubs, regatta organizers, and sailors, the CSA serves as a unified voice for the Caribbean sailing community, fostering collaboration and developing strategies to enhance participation in local and international sailing events. For more information visit: www.caribbean-sailing.com.