*New Year Celebrations* – Across the Caribbean Grand fireworks and beach parties across islands like Barbados, St. Lucia, and St. Barts. *Barbados Sailing Week* – Jan 15–21, Barbados World-class sailing festival with the Mount Gay Round Barbados Race. *Grenada Sailing Week* – Jan 25–30, Grenada & Carriacou Competitive racing and social events along Grenadian waters. *Crop Over Festival Preparations Begin* – Barbados Early events and competitions in... more...

*Roses & Romance: Valentine’s Week* – Caribbean-wide Luxury resorts host romantic packages, dinners, and sunset cruises. *Carnival Season (Trinidad & Tobago)* – Feb 7–10, 2026 Iconic parades, steelpan music, and colorful masquerade competitions. *Caribbean Multihull Challenge* – Jan 29–Feb 1, Sint Maarten Premier regatta for multihull yachts. *RORC Caribbean 600* – Feb 23–27, Antigua Legendary offshore race around 11 islands. more...

*St. Maarten Heineken Regatta* – Mar 5–8 Top-tier racing and vibrant entertainment. *St. Barth’s Bucket Regatta* – Mar 13–16 Prestigious large yacht regatta with exclusive social events. *BVI Spring Regatta & Sailing Festival* – Mar 23–29 Week-long sailing festival in the British Virgin Islands. *International Music & Jazz Festivals* – Jamaica, Cuba, Dominican Republic Concerts featuring local and global talent. more...

*Antigua Sailing Week* – Apr 22–26 Iconic regatta with intense racing and lively shoreside activities. *Easter Celebrations* – Across the Caribbean Processions, religious observances, and chocolate-themed family events. *Dominican Republic Carnival* – Apr 6–12 Colorful parades and cultural showcases in Santo Domingo. more...

*Martinique Yole Festival* – May 12–16 Traditional wooden boat races with vibrant cultural festivities. *Labor Day & Workers’ Festivals* – May 1 Island parades and local celebrations throughout the region. *St. Barth’s Art & Music Week* – Mid-May Exclusive exhibitions and soirées for collectors and tourists. more...

*Offseason / Summer Festivals* – June–August Smaller local regattas, eco-festivals, cultural workshops, and music events. *Caribbean Rum & Food Festivals* – Select islands Tasting events highlighting local cuisine and spirits. more...