The Top Five Caribbean Festivals

By: Maxine Sheppard

May 1, 2010

Regular vtravelled contributor David Whitley give us a run down of the greatest street parties from the sunny isles of Trinidad, Barbados, The Bahamas, Jamaica and The Cayman Islands. 

In the Caribbean an excuse is rarely needed to put on some music, have a drink and dance with abandon. But when the big festivals come around, the party takes on a whole new magnitude. Here are five of the Caribbean’s best booming, booty-shaking, bottle-clutching celebrations.


Where? Nassau, New Providence Island, Bahamas

When? Boxing Day and New Year’s Day

While most of the world is safely tucked in bed sleeping off a sherry and turkey overdose, Bahamians are taking to the streets in the most garish costumes imaginable. The first Junkanoo takes place in the early hours of Boxing Day morning and anyone staying near the parade route can forget about getting any shut-eye.

For hours, different crews – family or community groups that can number nearly a thousand – dance through the streets to the cacophonous sound of Goombay music. There are prizes available for the best crews, and preparation is taken incredibly seriously. A crew can take months sorting their costumes out.


Junkanoo © MissChatter on Flickr

Junkanoo © MissChatter on Flickr

Trinidad Carnival

Where? Port of Spain, Trinidad

When? Two days before Ash Wednesday (either February or March)

Many Caribbean islands have their own version of the Carnival – the one in Sint Maarten at the start of May is another great party, for example – but Trinidad’s Carnival is the daddy. It’s by far the biggest in the region, and it’s heaven for lovers of steel bands, calypso or soca.

Trinidadian Festivities © Roger McClean on

Trinidadian Festivities © Roger McClean on

The Trini Carnival is not just one big parade. There are launches, where the mas bands unveil their costumes; there are fetes which are essentially giant outdoor parties run by various companies and institutions; and there are panyards and calypso tents where the dirty dancing takes place.

The Carnival is not a locals-only affair. Visitors can buy a costume (be warned that it won’t leave much to the imagination) and join a mas band if they wish.

Reggae Sumfest

Where? Montego Bay, Jamaica

When? Mid-July

Imagine Glastonbury lasting for a week, take away the mud and concentrate on only one form of music and you’re just about there. Pretty much anyone who’s anyone in the world of reggae will be on stage, while the beach party on the opening Sunday sets the tone. If you didn’t think it was possible to be chilled and animated at the same time, then the Reggae Sumfest is proof that it happens.

Reggae Sumfest © Suki MacDonald Kapahi

Reggae Sumfest © Suki MacDonald Kapahi

Crop Over

Where? Barbados

When? July/August


In Barbados, a ceremony designed to celebrate the harvesting of the sugar crop has been turned into an excuse for a five-week long party. It all starts with the last of the season’s cane being delivered and the crowning of the most productive cane cutters as Crop Over King and Queen. This happens in the National Stadium at the end of a rowdy parade, and is followed up with an all-night session.



Pan In De City at Crop Over ©

Pan In De City at Crop Over ©


Over the course of 24 days of markets, concerts and heavy drinking, the festival then builds up to the Grand Kadooment. This involves another parade, bands and floats everywhere and, for visitors, the high chance of being swept up in it. Just accept the rum punch and go with the flow.



Pirates Week

Where? The Cayman Islands

When? Mid-November


In a more family-friendly alternative to the hedonism, drinking, bumping and grinding at other festivals, the Cayman Islands celebrates the bloodthirsty thieves of the sea.



Less bumping and grinding, more family fun © Pirates Week Festival

Less bumping and grinding, more family fun © Pirates Week Festival


Luckily, there’s no plank-walking or scourging during Pirates Week – it’s all good clean fun with sporting events, parades, costume competitions and food festivals. It kicks off with a “˜surprise’ pirate landing at George Town Harbour, when two ships full of locals in pirate garb rock up in a blaze of arrrrrrrrrrs and squawking parrots.


The last Saturday features the Trial of the Pirates, the Street Dance Finale and the inevitably doomed Cardboard Boat Race.

Thanks to MissChatter on Flickr for the Junkanoo photo and Suki MacDonald Kapahi for the Reggae Sumfest shot.

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Maxine Sheppard

Maxine is the co-editor of the Virgin Atlantic blog. Travel and music are her joint first loves, and despite having written for Virgin for more years than she cares to remember she still loves nothing more than jumping on a plane in search of new sights and new sounds.

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