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Caribbean Racing with the Danish Navy in St. Thomas, US VI Photo by Laurie Fullerton

Elevate Your Caribbean Charter Vacation: Attend a Regatta

Caribbean Yachting in 2023 is Worth Planning Now 

There is so much beauty in the Caribbean! What may be less well-known is the Caribbean regatta season, where sailors from around the world come to meet and compete. Charter yachts are available to race or to just watch from at some of these racing events which run from December through May each year.  Early planning is essential for this popular seasonal attraction. 

Each regatta uniquely reflects cultural influences that bring sailors and islanders together, whether it’s St. Maarten’s Dutch and French influence or the British flavor and yachting traditions of Antigua.  They give you a chance to meet locals who know and love these historic islands and who have long participated in these events.  

Regatta time gives a unique maritime twist to your yachting experience

Yes!  Our well-informed team guides clients each year through selecting a yacht and itinerary to get you to one of these regattas during your charter.  Here are a few favorite events. 

The 43rd Heineken Regatta St. Maarten March 2-5, 2023

In 1980, the 2023 Heineken Regatta St. Maarten started as the St. Maarten Regatta with a modest 12 sailboats participating. Three years later, in 1983, Heineken became a major sponsor of the St. Maarten Regatta and “Heineken” was added to the name of the event. In 2008, the record number of boats participating in the Heineken Regatta St. Maarten was 284 boats!

St. Maarten has both a Dutch and French flair, and their regatta is the famous kick-off event to the Caribbean racing season. There is so much to see and do in St. Maarten on both the Dutch and French sides, so any charter itinerary can include more choices, but for bragging rights, there is no better place to get introduced to Caribbean yacht racing than at “the Heineken”!

St. Maarten also features a unique opportunity to race a 12-meter yacht.  As past America’s Cup winners and contenders, the St. Maarten 12 Meter Regatta offers an exciting introduction to elite sailing competition and an adventure. There are head-to-head races (called “regattas”) daily, seven days per week. Ask Carol for more information!

St. Barths Bucket Regatta (March 15-19, 2023)

Feel the “Spirit of the Bucket”! The St. Barth’s Bucket Regatta is an opportunity for some of the world’s largest and most powerful sailing yachts to come together to race and socialize.  An exclusive event that also encourages tourists to participate and attend through yacht charters, the Bucket is the kind of event where the legendary singer and sailor Jimmy Buffet performs in an informal setting.

While the event features the J-Class boats like Velsheda and Ranger along with the Grand Dame des Mers class that includes the 197-foot PERSEUS 3, the beautiful Perini-Navi 183-foot ROSEHEARTY and the gorgeous L’Espirit des Mer 141-foot schooner COLUMBIA.

Many of the participating yachts are available for charter throughout the year and relocate to take advantage of temperate seasons and climate conditions.  You could spot the exact same vessel from a Spring Caribbean regatta plying the waters off Newport, RI a few months later.

USVI St. Thomas International Regatta (March 24 -26, 2023)

Formerly referred to by regional and international sailors as “the Rolex,” the St. Thomas International Regatta was – for over 40 years –  sponsored by Rolex, in part because the late CEO of Rolex and avid yachtsman Walter Fischer lived part of his time in St. Thomas and was an early member of the St. Thomas Yacht Club. As a sailor and enthusiast for the island, his company fully supported the Rolex brand until after his passing.  This gave the St. Thomas International Regatta the distinguished title of The Crown Jewel of Caribbean Racing. The event continues to occur around Easter Weekend each year, and it is renowned for the beautiful and laid-back setting at the yacht club on Cowpet Bay and for its incredible race courses and scenery.

Pat Bailey, co-director of the regatta, invites you warmly:  “For nearly 50 years of running regattas, we at the St. Thomas Yacht Club have provided our fellow sailors with beautiful island racing conditions and great courses, World Class Race Management and our renowned Virgin Island’s Hospitality and Fun. As we say at STYC, ‘We Love it Here, come join us and share the feeling!’”

BVI Spring Regatta (March 27 – April 2, 2023)

The BVI Spring Regatta and Sailing Festival is one of the Caribbean’s premier annual racing events. Its tagline is “Warm Water, Hot Racing”, celebrating its 50th year in 2023. It has long been one of the most popular events for US sailors who charter yachts for racing. The third largest regatta of its kind, it has developed a reputation for serious competition and professional race and event management.

Comprising 64 islands, the BVI is always an interesting and challenging place to sail, from the protected waters of the Sir Francis Drake Channel to the outer islands, with numerous natural marks which offer multiple possibilities to mix up the racing.

Throughout the week, Bitter End Yacht Club and Nanny Cay play host to participants with parties and prizes designed for those who sail and those that just want to have fun.

Antigua Classic Yacht Regatta (March 29-April 2, 2023) 

Back in the 60s, classic yachts in English Harbour had begun chartering, and the captains and crews challenged each other to a race down to Guadeloupe at the end of the charter season. From this informal race, Antigua Sailing Week was formed in 1967, and in those days all of the yachts were classic.

However, over the next 24 years, the classic yachts were slowly outnumbered by the faster, sleeker modern racing yachts. A small number of classics still racing in 1987 found themselves grouped with cruising Class 3 which was less than ideal for these hard-to-maneuver full-keeled vessels. And so it came about that Captains Uli Pruesse and Kenny Coombs hosted a meeting with other classic skippers onboard the magnificent schooner Aschanti of Saba and, several rums later, the Antigua Classic Yacht Regatta was born.

The Regatta has evolved into what it is today and features some of the most beautifully restored and maintained sailing yachts on the classic yacht circuit today. The unique events draw classic power yachts to spectate, charter and enjoy this festive and elegant event.

Les Voiles De Saint Barth (April 16-22, 2023)

A wonderful segue from St. Barths’ Bucket is the very popular Les Voiles de Saint Barth now in its 12th year.  Saint Barth’s stunning beauty and exceptional sailing conditions provide the perfect backdrop for competitive racing and après sailing fun and relaxation.

Les Voiles de St. Barth Richard Mille hosts five days of racing on diverse challenging coastal courses, a central Race Village for competitors to gather for morning cafés and evening concerts, plus Les Voiles’ signature mid-regatta “Day Off” at the famous Nikki Beach and the beach crew party, all while surrounded by the warm hospitality of Saint Barth’s classic French lifestyle. Multiple classes return each year led by the Maxis and Super Maxis, which now race under IRC (rules and regulations).

More than just a competitive regatta, the eco-friendly event invites racers and their guests to explore the best of Saint Barth’s fine dining, great shopping and incredible beaches. Throw in wall-to-wall Caribbean sunshine and a lay-day full of fun and games on white sands and in turquoise seas, and you have the perfect sailing regatta. St. Barths also boasts being one of the most “international” events, bringing a St. Tropez atmosphere to this French-speaking island.

Antigua Sailing Week (April 29 – May 5, 2023)

Antigua and Barbuda is a coveted destination for nautical events and throughout its history has maintained its reputation as one of the premier yachting destinations in the Caribbean. Due to its sheltered harbors, large number of anchorages, and abundant natural beauty, the islands present a haven for visitors seeking adventures on the water.

If you are looking for an amazing experience on both land and sea while adding a splash of epic partying to the mix, then look no further, Antigua Sailing Week is just for you! Additionally, now in its 12th year, the popular Antigua & Barbuda Hamptons Challenge Regatta was expanded this year to a four-day family festival. This festival features steel pan music,  family-friendly activities such as face painting and costumed dancers, and delectable Antigua and Barbuda cuisine. Up to 30 exhibitors from the islands will be at the John Steinbeck Waterfront Park, Sag Harbor.
This premiere sailing event along with its on-shore festival has cemented itself amongst the top three most prestigious regattas in the world and has held its momentum for nearly half a century, celebrating 54 years in 2023.

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