January 2025

Barbados Sailing Week

Organised by the Barbados Cruising Club in association with Barbados Tourism and Mount Gay Rum, Barbados Sailing Week is expected to once again attract top class competition. As well as three days of offshore races, which offer spectacular racing along the island’s stunning white-beach coastline, dinghy class races for under 16s, kiteboarding, wing foiling and remote-control boat events, competitors are also preparing to take on the headline event. The headlining 60nm Mount Gay Round Barbados Race gives crews a chance to win their skipper’s weight in rum if any of the 20 records are broken! Sounds great to us! Contact us now to discuss your racing yacht charter for the event, there will be something for everyone!
10 - 22 Jan
All Day
Barbados Cruising Club

Pineapple Cup Race

Consisting of six challenging days of top class racing in, what are regarded as the best sailing conditions in the world, the regatta has developed into a world-class event." Get for the ultimate destination offshore race!  The Pineapple Cup is one of the oldest offshore races in the USA, the 811nm course takes your from Miami to Montego Bay Jamaica. We’re very excited to be able to offer you the opportunity to race on an exciting offshore performance racing boat!
25 - 31 Jan
All Day
Montego

Grenada Sailing Week

Grenada Sailing Week, a six day regatta, kicks off the start of the racing season in the southern Caribbean with four days of exciting racing, all in the beautiful blue waters of Grenada. The race committee have put together a thrilling mix of windward and leeward courses encompassing the different challenges Grenada’s coast has to offer. From the shifting winds on the protected west coast to the gustier winds and open waters on the south, there is something for everyone in this regatta. Charter options vary and there will be a racing yacht for every team and skill level!
26 - 31 Jan
All Day
St George's

Caribbean Multihull Challenge

The ever growing Caribbean Multihull Challenge takes place in the waters of St Maarten, an island known for great sailing! The Sint Maarten Yacht Club, organisers of this new regatta, are acknowledging the rapid growth in popularity of multihulls for racing; and the technological advances in the industry enabling the newer boats to be safe and comfortable but extremely fast in all kinds of winds. The racing in this new event will be spirited, highly competitive, and full of fun surprises, including more fast reaching targets, rather than windward-leeward type races, in order to suit multihull racing!
31 Jan - 02 Feb
All Day
Simpson Bay
February 2025
March 2025

St Maarten Heineken Regatta

Experience the thrill of the St. Maarten Heineken Regatta with LV Yachting! Join us for the Caribbean’s most electrifying regatta, where racing and vibrant island life come together in a legendary event. The St. Maarten Heineken Regatta attracts sailors and enthusiasts from around the world for four unforgettable days of intense racing, set against the crystal-clear waters and warm winds of the Caribbean. Whether you’re a seasoned racer or looking to jump into competitive sailing for the first time, LV Yachting offers premier charter options to suit your experience and ambitions. After the racing, the shores of St. Maarten come alive with unforgettable festivities, music, and celebration, adding to the regatta's reputation for "Serious Fun." Let us help you secure your spot on a race-ready yacht, complete with experienced crew options. Explore the St. Maarten Heineken Regatta and make your mark in one of the world’s top sailing events!
06 - 09 Mar
All Day
Simpson Bay

St Barth’s Bucket

In 1995, the beautiful island of St Barths hosted its first Bucket Regatta and it has done so in March every year since then. Although the size of the yachts and competing fleet has grown significantly, the spirit of the event has remained unchanged. In recent years, 40 or more superyachts have gathered to compete for the Bucket. As the Bucket Regatta has evolved, the organisers have kept a tight focus on maintaining the original camaraderie and non-commercial spirit of the event. It was, and still is, an event conceived and hosted purely for the pleasure and enjoyment of the sailing superyacht owner. There is no other regatta of magnitude on the superyacht racing circuit with the same goals, and the event organisers consider themselves the stewards of a most worthwhile tradition. Every year, invitations are extended to like-minded individuals. If you are looking at taking part in this spectacular regatta, please contact us now!
13 - 16 Mar
All Day
Gustavia

St Thomas International Regatta

The St Thomas International Regatta is a crown jewel in the Caribbean racing season, offering sailors from around the world three days of unparalleled racing. The courses weave through the picturesque cuts and cays of the U.S. Virgin Islands and the excellent racing is topped off by live music, good food and camaraderie between the competitors ashore at the St Thomas Yacht Club. With all the boats anchored in Cowpet Bay, all competitors come together before and after racing giving the regatta a fantastic vibe. Individual Spaces are available on the following yachts. Select to find prices and information.
27 - 31 Mar
All Day
St Thomas
April 2025
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