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(COURTESY ANTIGUA SAILING WEEK) 

A generation ago, many competitors would happily sleep on deck, pack their own food, and compete with basic gear. Now, race campaigns are more performance-driven and logistically complex and expectations lean toward air-conditioned shore digs, dockside access, professional crew, and dedicated support teams.

(COURTESY ANTIGUA SAILING WEEK) A generation ago, many competitors would happily sleep on deck, pack their own food, and compete with basic gear. Now, race campaigns are more performance-driven and logistically complex and expectations lean toward air-conditioned shore digs, dockside access, professional crew, and dedicated support teams.

Caribbean Regattas Fight a Turning Tide 

Caribbean Compass by Caribbean Compass
October 1, 2025
in Regattas & Rallies
Reading Time: 9 mins read
A A

By Zoë Carlton  

The crowds have dispersed, the sails are furled, and the marinas are quiet again — Antigua Sailing Week (ASW) has wrapped up for another year. And it’s time to set the record straight. 

Criticism over declining participation at ASW — 53 boats in 2025 — misses the broader picture. Yes, numbers are down from its golden era of over 150 entries. this isn’t just an Antigua problem. There are no regattas with these halcyon numbers now; it is a reflection of challenges facing sailing worldwide. 

Under Pressure 

The Caribbean Sailing Association (CSA) hosts an annual conference that serves as a crucial forum for assessing the health of the region’s sailing industry. It brings together regatta organizers, race officials, and measurers to share best practices and chart a course forward. A recent CSA study confirmed what insiders have long known: racing participation is down across the region. In 2006, around 820 boats raced in seven Caribbean regattas. By 2025, that number has dropped to about 527 — spread over twice as many events. That’s a tighter race for entries. 

As Cayley Smit, director of the BVI Spring Regatta, puts it: “The numbers of boats have definitely decreased over the long term but we are seeing a steady uptick in participation. We had a spectacular regatta this year with plenty of wind, fantastic racing and an incredible, warm vibe in the village. There are many reasons for changes in the number of boats racing in the Caribbean, but it’s not the sailing conditions — our courses are a dream for racing. We have no control over delivery costs, stacked racing calendars, or flight prices, but we will consistently deliver a quality regatta. Our BVI community works together to continuously improve on our delivery, professional race management, ease of travel, and engaging strong partners who care about sailing.” 

Her comments echo the reality across the Caribbean: regatta organisers are fighting global economic and logistical headwinds, but they remain committed to delivering world-class racing experiences. 

Multitude of Factors 

Once, sailors could hop among three or four Caribbean regattas in a season. Now, tighter budgets, rising climate awareness, and a packed global sailing calendar force hard choices. Take Les Voiles de St. Barth — cancelled in both 2024 and 2025 due to sponsorship gaps. The Heineken Regatta in St. Maarten drew around 80 boats. Grenada hosted 30–40. Barbados? Just 15–20. 

In the early days of Caribbean regattas, most boats stayed local — crews lived aboard, anchored out, and raced with less concern for weight or logistics. Fast forward to today, and it’s a different fleet entirely. Top racing yachts now transit the Atlantic on ship decks to chase both the Caribbean winter and European summer circuits. That means timing is tight — late-season events like ASW face real pressure as boats rush to cross back. Add to that the modern demand for dock access and shore accommodations, and infrastructure becomes a deciding factor. 

While the boats themselves are faster and more technical, the culture of competitive sailing has shifted. Race campaigns are more performance-driven, logistically complex, and crew-dependent than ever before. A generation ago, many competitors would happily sleep on deck, pack their own food, and compete with basic gear. Today, expectations lean toward air-conditioned shore digs, dockside access, professional crew, and dedicated support teams. This shift has placed logistical and financial pressure on regattas — and especially those like ASW that fall late in the season. 

Antiguan businessman Robbie Ferron, who has been sailing in ASW for many years, points out that a review of Caribbean regattas shows there are no events hosting 150 boats anymore. Antigua, he says, “remains the region’s leader, but like others, it has adapted to shifting trends.” 

Today’s regattas are increasingly specialised, and Antigua reflects that with a trio of events: the Classic Yacht Regatta, the long-distance RORC Caribbean 600, and the inshore-focused ASW. The Superyacht Challenge also attracts international boats. The old model of a large, mixed-fleet regatta — once the foundation of ASW’s 150-boat heyday — has largely disappeared. Adds Ferron, “The time slot held by ASW to date has eliminated the chance of entries by a class of boat that requires to return to the UK or Europe earlier than would be possible when entering ASW. [none of this] is caused by the present management of ASW.” 

Timing is indeed critical. For years, organisers have suggested moving ASW earlier to catch the RORC boats and racers still on the island. By the end of April, many yachts have already left for Europe or the U.S. to qualify for major summer events like Fastnet or Newport–Bermuda. ASW President Alison Sly-Adams believes this timing challenge is the single biggest factor driving numbers down. 

Meanwhile, as the yachting community shifts toward more cruisers and fewer pure racers, ASW has begun experimenting. A new “fun regatta” and pursuit-style cruising events were added in 2025 along with an early new event to focus on the race campaigns heading out early. While still in the early stages, the strong feedback shows clear potential — proof that ASW is embracing innovation and ready to grow. 

(COURTESY ANTIGUA SAILING WEEK) With a few exceptions, regatta participation is down across the islands, and though organizers are fighting global economic and logistical headwinds, they remain committed to delivering world-class racing experiences.

A Cluster of Excellence 

Despite the regional decline, Antigua — small but mighty — hosts four major international regattas. Compare that to most Caribbean islands, which typically host just one. 

Antigua, as tourism minister Charles Fernandez notes, is the “Mecca of 

sailing.”  Sly-Adams puts it even more simply: “Antigua has always been the heart of Caribbean yachting.” 

Antigua’s share of the Caribbean’s total racing entries has grown — from 31percent to 39 percent over the past two decades. That’s not just resilience; that’s leadership. 

Comprehensive Support Infrastructure 

Antigua offers robust shore and on-water support. The Antigua and Barbuda Search and Rescue (ABSAR) team, along with local divers, ensures safety and assistance during the regatta. This comprehensive support contributes to Antigua’s reputation as a premier sailing venue. 

Diverse Sailing Events 

Antigua is not solely about international racing. As well as those who just come to enjoy Antigua itself, the island hosts events like the Salty Dawg Rally, the Atlantic Rally for Cruisers (ARC) boats sail-in, the Oyster World Rally and new this year, the Mini Globe Race. These events attract a mix of cruisers and racers, showcasing Antigua’s versatility in catering to different sailing communities. 

Shifting Landscape 

Today’s sailors are different. Many now prefer high-prestige, tightly run events like the RORC 600 — faster, more intense, and easier to schedule. Ironically, the success of the Caribbean 600 has created new challenges for ASW: boats arrive for that race,  leave before Sailing Week begins to race elsewhere. Notwithstanding, ASW 2025 welcomed boats from over 20 countries — and included significant Antiguan-owned participation. 

Critics are quick to compare 2025’s 53 boats to 2024’s 88 and 750 crew. Despite this, dock master Tommy Patterson points out that the marinas have not seen a noticeable drop in boats over the 2025 season. This narrow view ignores the overall picture and long-term global trends: fewer racing yachts, more cruising sailors, and more curated sailing experiences.  

Anchored in Community 

Behind the scenes, many local voices are also calling for deeper community inclusion in the regatta’s planning — ensuring ASW stays grounded in its roots while innovating for the future. 

Local participation remains strong. While the regatta may no longer stretch to the farthest shores of Antigua, 40 young Antiguans joined visiting boats as crew this year, and around 10 Antiguan-owned boats raced in the event.  

The Economic Lifeblood 

ASW is more than a regatta — it’s an economic lifeline. “We welcome the sailors — this is our last chance to boost our season,” one restaurateur said. Taxi drivers, market vendors, and hoteliers feel the lift, too. Andrew Dove of North Sails noted, “ASW always brings in more business.” Its impact radiates far beyond English Harbour. 

A Government-Backed Future 

Although the government has signalled plans to take ASW “in-house,” recognising its cultural and economic value, the event is still owned by Antigua Barbuda Hotels & Tourism Association, with a licence in place until May 2026. If executed well, more government input could better align the regatta with national tourism goals. But it must preserve the expertise, relationships, and energy built by the current ASW team. 

“There’s a conversation to be had with the government about what Antigua wants ASW to be,” says Sly-Adams. “Through 2024 and right up to before 2025 ASW has engaged with stakeholders and put forth potential solutions to the issue. Clearer and unified vision, better marketing and strong collaboration are critical to the future success.” 

Antigua Yacht Club: The Beating Heart 

The Antigua Yacht Club is the cornerstone of the island’s sailing legacy. Financially constrained, yet still host to all major international regattas, its role cannot be overstated. A glimmer of progress came this year with a new three-year agreement between AYC and RORC for the Caribbean 600 — proof that solutions are possible. 

To remain a true international sailing mecca, Antigua needs a yacht club equipped to meet global standards. A prolonged financial dispute with the South West Properties Marina and Resort Ltd has left the Antigua Yacht Club (AYC) unable to invest in its facilities for over six years. But make no mistake: to support Antigua’s sailing future as a world-class destination, serious investment in the AYC as a world-class yacht club is not optional. 

Infrastructure: The Unseen Race 

It is not just down to AYC or ASW. The wider infrastructure must support the event. In 2025, on the eve of ASW, the main road leading into the Yacht Club was dug up for repairs and simply left — prompting loud (and colourful) complaints from visiting crews. Parking in the area remains a major challenge. Moorings and jetties must be made safe and maintained before, not during, the regatta. 

Cost is another challenge. A recent travel survey cited by The Daily Mail, named Antigua the second most expensive tourist destination in the world. Visiting sailors often cite the high cost of food, mooring, accommodation, and transport.  

On Course 

ASW still combines serious competition on the water with warmth and welcome ashore. From elite racers to curious first-timers, everyone is invited. 

And Antigua is not alone in this. Across the Caribbean, from the BVI Spring Regatta to the Heineken in St. Maarten, organisers are adapting — working harder than ever to overcome delivery costs, crowded calendars, and shifting sailing cultures. This is a regional fleet facing the same winds, and in true sailor fashion, they are trimming their sails and finding a way forward. 

Whatever course ASW charts next, one thing is clear: the heart of Caribbean yachting still beats strong in Antigua — and it beats in time with the whole region. This isn’t just a regatta. This is a community of islands proving, year after year, that the Caribbean is still one of the greatest places in the world to race a boat. 

Zoe Carlton is a journalist and media personality in Antigua telling stories of life in the Caribbean on and off the water.  

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