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January 2019

Barbados Sailing Week

January 16, 2019 - January 24, 2019

The Caribbean race season’s opening regatta is now to be known as Barbados Sailing Week, which replaces its former title, the Mount Gay Round Barbados Series. 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.

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Grenada Sailing Week

January 27, 2019 - February 1, 2019

In idyllic sailing conditions, a challenging variety of shorter up/down around the buoys and longer reaching coastal courses off Western and Southern Grenada, ensures there is something for everyone in this regatta.

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February 2019

Swan Rolex Caribbean Cup

February 27, 2019 - March 3, 2019

2019 marks the fourth edition of the biennial Rolex Swan Cup Caribbean, held at the Yacht Club Costa Smeralda’s new clubhouse in the sailing paradise of the British Virgin Islands.

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St Maarten Heineken Regatta

February 28, 2019 - March 3, 2019

This Regatta is the largest warm water regatta in the world and offers a great combination of challenging races and fantastic parties, keeping with the event’s motto “Serious Fun”!

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March 2019

St Barths Bucket

March 21, 2019 - March 24, 2019
Gustavia Virgin Islands (British) + Google Map

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.

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St Thomas International Regatta

March 22, 2019 - March 24, 2019
St Thomas Virgin Islands (U.S.) + Google Map

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.

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BVI Spring Regatta & Sailing Festival

March 25, 2019 - March 31, 2019
Royal BVI Yacht Club Virgin Islands (British) + Google Map

The week long Spring Festival and Regatta are two great events rolled into one, including some beautiful cruising, competitive racing and serious fun on and off the water!

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April 2019

Les Voiles de Saint Barth

April 14, 2019 - April 20, 2019
Gustavia Virgin Islands (British) + Google Map

St Barth is possibly the most chic island in the Caribbean. The regatta was founded in 2010 and is growing in popularity every year. Les Voiles de St Barth is an amazing rendezvous of yachts

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Antigua Sailing Week

April 28, 2019 - May 3, 2019
English Harbour English Harbour, Antigua And Barbuda + Google Map

From small beginnings, Antigua Sailing Week has developed into a world-class event and now includes an Ocean Series for boats that prefer ocean racing.

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June 2019

Giraglia Rolex Cup

June 7, 2019 - June 15, 2019

The Giraglia Rolex Cup, is one of the most renowned offshore races in the Mediterranean. Starting with feeder races from Sanremo or Marseille, the fleet will gather in the Chic…

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