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  Barbados Sailing Week
  January 15, 2026
  Barbados
  The Caribbean race season’s opening regatta, the Round Barbados Sailing Week, formerly Mount Gay Round Barbados Series, is a 8-day . . . . . .
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  Antigua Carnival
  July 25, 2026
  Antigua
  Antigua Carnival is one of the hottest events which takes place each summer, bringing a high-energy explosion of music, mas, . . . . . .
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  Cayman Cookout 2026
  January 14, 2026
  Cayman Islands
  Set against the stunning backdrop of Seven Mile Beach on Grand Cayman, Cayman Cookout 2026 returns for six days of . . . . . .
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  Lucian Carnival 2026
  July 1, 2026
  Saint Lucia
  Lucian Carnival is one of the island’s biggest events, so it is no surprise that this carnival grows every year. . . . . . .
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  BVI Emancipation Festival
  July 13, 2025
  British Virgin Islands
  Celebrate the British Virgin Islands’ cultural history and freedom from colonialism. . . .
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  Summer Sizzle BVI
  July 23, 2025
  British Virgin Islands
  Inspired by New York Fashion Week, Executive Producer Terry Donovan created Summer Sizzle BVI in 2009 as an event aimed . . . . . .
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  St Maarten Carnival
  March 14, 2025
  St. Maarten
  Every spring, the island of St. Maarten transforms into a vibrant tapestry of color, music, and culture as it celebrates . . . . . .
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  SXM Festival
  March 12, 2025
  St. Martin
  The SXM Festival, scheduled from March 12 to 16, 2025, on the picturesque island of Saint Martin, promises an unparalleled . . . . . .
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Race

Barbados Sailing Week

Barbados Sailing Week

Showing

The Caribbean race season’s opening regatta, the Round...

Antigua Superyacht Challenge 2026

Antigua Superyacht Challenge 2...

Upcoming

The 15th edition of the Antigua Superyacht Challenge is set ...

St. Maarten Heineken Regatta

St. Maarten Heineken Regatta

Upcoming

Get ready to experience the ultimate Caribbean sailing event...

Sandy Lane Gold Cup

Sandy Lane Gold Cup

Upcoming

One of the most prestigious events in the Eastern Caribbean ...

Aruba Hi-Winds

Aruba Hi-Winds

Upcoming

Aruba Hi-Winds is the largest Windsurfing tournament of its ...

Tortola Torture

Tortola, British Vir...

Tortola Torture

Upcoming

The Tortola Torture, an ultramarathon that has etched its na...

SVG Sailing Week 2026

SVG Sailing Week 2026

Upcoming

Set your sights on turquoise waters, sun-drenched shores, an...

Antigua Sailing Week 2026

Antigua Sailing Week 2026

Upcoming

One of the most prestigious sailing regattas in the world, A...