3 January 2026
January 2026
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New Year Celebrations – Across the Caribbean
Grand fireworks and beach parties across islands like Barbados, St. Lucia, and St. Barts.
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Barbados Sailing Week – Jan 15–21, Barbados
World-class sailing festival with the Mount Gay Round Barbados Race.
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Grenada Sailing Week – Jan 25–30, Grenada & Carriacou
Competitive racing and social events along Grenadian waters.
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Crop Over Festival Preparations Begin – Barbados
Early events and competitions in anticipation of summer festival.
February 2026
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Roses & Romance: Valentine’s Week – Caribbean-wide
Luxury resorts host romantic packages, dinners, and sunset cruises.
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Carnival Season (Trinidad & Tobago) – Feb 7–10, 2026
Iconic parades, steelpan music, and colorful masquerade competitions.
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Caribbean Multihull Challenge – Jan 29–Feb 1, Sint Maarten
Premier regatta for multihull yachts.
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RORC Caribbean 600 – Feb 23–27, Antigua
Legendary offshore race around 11 islands.
March 2026
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St. Maarten Heineken Regatta – Mar 5–8
Top-tier racing and vibrant entertainment.
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St. Barth’s Bucket Regatta – Mar 13–16
Prestigious large yacht regatta with exclusive social events.
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BVI Spring Regatta & Sailing Festival – Mar 23–29
Week-long sailing festival in the British Virgin Islands.
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International Music & Jazz Festivals – Jamaica, Cuba, Dominican Republic
Concerts featuring local and global talent.
April 2026
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Antigua Sailing Week – Apr 22–26
Iconic regatta with intense racing and lively shoreside activities.
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Easter Celebrations – Across the Caribbean
Processions, religious observances, and chocolate-themed family events.
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Dominican Republic Carnival – Apr 6–12
Colorful parades and cultural showcases in Santo Domingo.
May 2026
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Martinique Yole Festival – May 12–16
Traditional wooden boat races with vibrant cultural festivities.
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Labor Day & Workers’ Festivals – May 1
Island parades and local celebrations throughout the region.
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St. Barth’s Art & Music Week – Mid-May
Exclusive exhibitions and soirées for collectors and tourists.
June–August 2026
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Offseason / Summer Festivals – June–August
Smaller local regattas, eco-festivals, cultural workshops, and music events.
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Caribbean Rum & Food Festivals – Select islands
Tasting events highlighting local cuisine and spirits.
September 2026
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Klein Curaçao Race – Exact dates TBD
Offshore sailing challenge from Curaçao to Klein Curaçao.
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Oktoberfest Caribbean – Various islands
Beer, music, and cultural events celebrating local and European fusion.
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Heritage & Independence Day Celebrations – Select islands
Cultural events showcasing history, dance, and local pride.
October 2026
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Aruba Regatta – Oct 18–20
Competitive races featuring dinghies, yachts, and windsurfing.
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Diwali / Festival of Lights – Trinidad & Tobago, Guyana
Traditional celebrations with fireworks, music, and sweets.
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Halloween & Caribbean Costume Festivals – Oct 31
Parties and cultural celebrations with Caribbean flair.
November 2026
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Golden Rock Regatta – Nov 6–10, St. Eustatius & nearby islands
Sailing festival celebrating historic trade routes.
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Curaçao Regatta – Exact dates TBD
Community regatta featuring various boat classes.
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Jazz & Music Festivals – Bahamas, Dominican Republic
International music events for jazz and classical music lovers.
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Day of the Dead Observances – Caribbean-wide, select communities
Cultural ceremonies honoring ancestors.
December 2026
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Antigua Charter Yacht Show – Dec 4–9
Showcase of luxury charter yachts for industry professionals.
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Christmas & Boxing Day Festivities – Across the Caribbean
Family gatherings, beach parties, parades, and fireworks.
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New Year Preparations & Parties – Dec 26–31
Grand island celebrations, beachfront concerts, and luxury events.
Notes for Readers:
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Dates may shift slightly depending on organizers or weather conditions.
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For sailing regattas, check official websites for race notices and registration.
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Cultural festivals often include smaller island-specific celebrations beyond these highlights.
