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Caribbean Festivals and Events Guide

Celebration is a way of life on many tropical islands

Charting a course for the Caribbean? Chances are you'll discover something beautiful to celebrate. It's a way of life here. Rain or shine, summer or winter, there's always a parade, music festival or sailing regatta somewhere. And while some festivals are all about the fun, some celebrate the art and creativity of the local culture.

If you're traveling high season (December to April) Caribbean FestivalsCaribbean Festivalsyou're almost guaranteed one on the island of your choice. Off season is surprisingly ripe for fun as well - you'll just have to look harder.

If you're all about the celebrating (or just love to see art celebrated), have a look at some of our favorite ways to make merry:


When: First rush begins on Boxing Day, second is New Year's Day and the third is in the summer - begins at 3:00 am and wraps up at noon
Where: Nassau, Bahamas
What: Fiercely competitive parades that involve locals competing for the title of the best costumes, music and dances.

New Year Sailing Regatta

When: First week of January
Where: Montagu Bay, Bahamas
What: A colorful sailing regatta of 30-40 ships all built in the area - they compete across 3 classes.

Barbados Annual Jazz Festival

When: Second weekend of January
Where: Various venues throughout the island
What: Talent from Canada, United States, Europe and all over the Caribbean perform live all weekend long.

San Sebastian Street Festival San Juan

When: Last week of January
Where: Old San Juan
What: The Mardi Gras of the Caribbean - revel in street parties by night; stroll the same streets filled with artisans by day.

Aruba Carnival

When: First week of February
Where: Oranjestad & San Nicolas
What: Parade after parade and parade - this is the place to be if you like to be in the center of all the fun.

Santiago's Carnival

When: Every Sunday in February with bonanza the first weekend in March
Where: Throughout the Dominican Republic and finishing up in Santo Domingo
What: Intense competition between two groups - La Joya and Los Pepines. Each spends much of the year preparing and making horns and weapons made of inflated cow bladders attached to long cords.

Port of Spain's Carnival

When: Mid February
Where: Queen's Park Savannah, Trinidad
What: A celebration of art and culture unlike anything you've ever experienced before - trust us.

Crop-Over Festival

When: Mid-July
Where: Barbados
What: A three-week festival that marks the end of sugar-cane season - begins with calypso competitions and wraps up with a massive parade.

Carnival, Santiago de Cuba

When: Last week of July
Where: Santiago, Cuba
What: The oldest and biggest celebration of Spanish culture in the Caribbean. This carnival is a decadent feast for all your senses.

Fiesta de Santiago Apostal

When: Last 5 days of July
Where: Aldea Loiza, Puerto Rico
What: A celebration of African and European ancestry with amazing drum ensembles, masks and traditional saint costumes.

Carnival, Antigua

When: Last week of July
Where: St. John's, Aruba
What: Evening street parties (jump-ups), calypso music, masqueraders, floats and fabulous food to sustain you through all the fun.

Reggae Summerfest

When: July
Where: Montego Bay, Jamaica
What: Bob Marley and Rastafarians from all over the world congregate every July to jam it up for a full week of fun.

Bermuda Music Festival

When: October
Where: Royal Navy Dockyard, Bermuda
What: A mix of international and local artists perform on a stage built over the water.

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