For decades, the Caribbean racing season has attracted some of the world’s best sailors, fastest boats and most iconic events. From offshore races to inshore regattas and cruising rallies, the region has earned its reputation as one of the premier sailing destinations on the planet.
But today’s Caribbean sailing scene is about much more than chasing a single regatta trophy.
A growing calendar of interconnected events, new race formats, cruising rally opportunities, and season-long awards is creating more ways than ever for sailors of all experience levels to enjoy the Caribbean sailing season. Whether the goal is to campaign for a championship, explore new islands under sail, or simply enjoy some friendly competition with like-minded crews, the Caribbean Sailing Association (CSA) is helping create a season that truly offers something for everyone.
At the heart of this evolution is the reformatted Five-Year CSA 2027-2031 racing calendar. The schedule now condenses the core racing season into an action-packed four-month-long series, making it easier for teams to plan campaigns across multiple events while still allowing plenty of flexibility for those who prefer to pick and choose their adventures.
‘The calendar provides a roadmap but it’s really a chooseyour- own-adventure story,’ says CSA vice president Saskia Revelman. ‘You can race every other week on a different island and create a non-stop Caribbean circuit, or you can select the events that suit your boat, your crew and your cruising plans.’
That flexibility has inspired a growing collection of season-long trophies that recognise excellence across multiple events rather than a single week of racing.
The Budget Marine Windies Multihull Trophy, the multihull version of the Traveller’s Trophy, encourages multihull owners to participate in smaller and more events. The trophy is awarded to the best-performing multihulls across five of the region’s 14 multihull-class events, including: Barbados and Grenada Sailing Weeks, RORC race events, BVI Spring Regatta, and the dedicated Caribbean Multihull Challenge.
The trophy reflects the growing strength of Caribbean multihull racing and rewards consistency across three distinct venues and race formats. This season’s winners included Sophia in the over-60ft division and the multi-time winner, Leopard 50 La Novia, in the under-60ft category.
Another new addition to the trophy mantel, the FKG Inshore-Offshore Trophy highlights the unique diversity of Caribbean racing. Presented at the St Maarten Heineken Regatta, the award recognises the team that performs best across both the RORC Caribbean 600 offshore race and the Regatta’s inshore racing series.
The concept celebrates the versatility of both sailors and boats versatility. Success requires a crew capable of handling one of the world’s most challenging offshore course races before quickly transitioning to tactical inshore competition. The inaugural trophy went to the nimble team aboard J/125 Jackknife.
For monohull teams looking to commit to a broader campaign, the Traveller’s Trophy recognises the best overall performance across the CSA series. To celebrate the charter-driven programmes, an additional CSA Traveller’s Trophy for charter teams was established this year. That trophy was won by Panacea X, a successful charter programme led by owner Katy Campbell. By welcoming new sailors and rotating crew members throughout the season, Panacea X has demonstrated that competitive success and inclusivity can go hand in hand.
‘We’ve been running Panacea X on the Caribbean circuit since bringing her across the Atlantic from Europe in early 2022,’ said owner and skipper Katy Campbell. ‘We came for the sunshine and stayed for the racing! The CSA circuit offers such a great range of events across the whole windward-leeward island chain.’
‘Every year we get this fantastic combo of lovely cruising and delivery trips to explore new anchorages and different sides of each island… and then great racing with awesome conditions within a really wonderful sailing community.’
The winner of the Traveller’s Trophy, now specifically for owner-driven teams who compete with a largely consistent crew through the season, was Donald Nicholson’s Apollo, a team that exemplifies the commitment and continuity that remain at the heart of amateur racing.
These season-long awards are changing how sailors think about participation. Rather than focusing on a single regatta, crews can now build campaigns around a collection of events and know that strong performances throughout the season will be recognised. Just as importantly, the variety of trophies means there are more opportunities for different boats and teams to find success.
For some, that means competing for overall series honours. For others, it may be a multihull championship, an offshoreinshore combination trophy, a private team award, or one of the many special prizes offered by individual events.
Many regattas now include awards that recognise youth development, women’s participation, sportsmanship, team spirit and community engagement. The legendary “Serious Fun!” prize at the St Maarten Heineken Regatta remains a perfect example of the Caribbean’s unique blend of high-performance racing and celebration back ashore.
This year’s “Serious Fun!” prize was awarded to an all-female team of sorority sisters from the Netherlands. Aged 27 to 67, the “Magnificent 10,” as they called themselves, brought the true regatta spirit from competitive days on the water to long nights of celebration back ashore. Their beer-themed matching dresses won recognition at the Bridge Show and ultimately the prize for embodying the spirit of the St Maarten Heineken Regatta.
The calendar itself continues to evolve as organisers explore new ways to connect sailors with destinations and experiences. For the 2027 season, the CSA calendar welcomes Bequia Easter Regatta and Round Martinique, adding two distinctive events in the Windward Islands to an already diverse schedule.
St Thomas International Regatta will also return with a new April date and an innovative format that combines rally-style cruising, traditional buoy racing, inshore competition, and “around-the-rocks” course – where, in true Caribbean fashion, the rocks happen to be islands.
Elsewhere, Antigua has emerged as a model for innovation with two complementary events that cater to different audiences. The Antigua Racing Cup has quickly established itself as a new opportunity for dedicated racing teams, hosted between the St. Maarten Heineken Regatta and the BVI Spring Regatta.
Antigua Sailing Week, meanwhile, has evolved into a destination-focused experience that celebrates sailing around the island while honouring the competitive spirit that has defined the event for decades. Together, they illustrate a broader trend throughout the Caribbean: creating more pathways into the sport rather than expecting every team to fit a single model.
The CSA is also working to attract top international competition while maintaining the accessibility that has long defined Caribbean racing. This past season, several major events offered dual scoring under both CSA and IRC ratings, giving teams additional opportunities to compete and compare performances on an international stage.
‘Offering IRC scoring alongside CSA racing provides greater opportunities for international competitors while maintaining the accessibility and inclusiveness of the CSA system that Caribbean sailors value,’ says CSA president Bastien Pouthier. The CSA’s role as the IRC Caribbean Rating Authority further streamlines the process for teams seeking IRC certificates in the region, ensuring that measurement, documentation and scoring are efficient and consistent throughout the season.
For visiting teams, the system provides a straightforward pathway into Caribbean competition. For local sailors, it opens the door to broader international benchmarking while preserving a rating rule designed specifically for the realities of regional racing.
Ultimately, this balance between tradition and innovation is what makes today’s Caribbean sailing calendar so compelling. The region still offers the legendary races, world-class competition and picture-perfect venues that have long attracted sailors from around the globe. But it also offers something more.
It offers choice. Campaign for an overall series title, chase a multihull championship, combine offshore and inshore racing, compete with a private owner-driven team, join a charter programme, participate in a rally, or simply follow the trade winds from island to island with a few friendly races along the way.
The CSA’s role is to bring these opportunities together into a cohesive season that benefits sailors, events and host destinations alike. The calendar may provide the roadmap, but how you sail the Caribbean is entirely up to you.
