Discovering Caribbean events

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Caribbean holidays are not just beaches and cocktails. They’re a rich calendar of events that celebrate music, culture, food, and history. Across the islands, festivals bring streets alive with rhythm, colour, and energy. If you love vibrant parades, island flavours, and unforgettable crowds, you’ll find something that fits your travel plans.

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Festival seasons vary, but the heart of the Caribbean’s party is the people. Expect warm welcomes, local costumes, and performances that showcase generations of artistry. Whether you’re visiting for a week or a longer break, timing your trip with a festival can make your holiday truly memorable.

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Popular festivals by island

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• Crop Over (Barbados) – a summer celebration culminating in Grand Kadooment, with calypso, soca, and vibrant costumes.

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• Trinidad Carnival (Port of Spain) – renowned for its mas bands, steelpan, and soca, with events leading up to the big parade.

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• Reggae Sumfest (Montego Bay, Jamaica) – a music festival showcasing Jamaica’s reggae and dancehall stars.

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• Saint Lucia Jazz & Arts Festival – a refined mix of jazz, arts, and Caribbean culture.

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• Saint Vincent and the Grenadines’ Vincy Mas – lively carnival scenes with street parades and costumes.

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In addition to these headline events, many islands host smaller street parties, food fairs, and village fetes. These are fantastic chances to sample local dishes, meet residents, and learn about traditional crafts.

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What to expect and how to join

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• Vibrant parades with elaborate costumes and marching bands.

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• Street parties that spill into late night with live music and dancing.

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• Food stalls offering regional dishes like jerk, curries, and fresh seafood.

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• Opportunities to buy crafts, beads, and traditional fabrics.

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Planning tips

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1. Check the festival calendar early and book flights and accommodation soon.

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2. Look for official ticket outlets to avoid scams and inflated prices.

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3. Choose a central base near the main parade routes or venues.

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4. Pack lightweight clothing, sun protection, and comfortable footwear.

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5. Respect local customs and safety guidelines in crowds.

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For more detailed guidance on a particular festival or island, our travel experts can help tailor your trip. If you’d like further information or help with booking a holiday to that destination, use the live chat box at the bottom of this page.

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