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Pirates, Masks And Calypso - Caribbean Festivals

24 June 2014

Pirates on a Ship

The Caribbean is the world’s top cruising destination, and once you’ve been there you’ll have no confusion as to why. Endless blue water which sparkles aquamarine and sapphire until a blazing sun, welcoming people with fascinating cultures, and islands which are the definition of tropical paradise: there’s nowhere better in the world. However, if you visit during the right time of year, you’ll understand that the Caribbean has even more to offer than it might appear at first glance. Exciting festivals, alive with music and laughter, open their arms to everyone - young and old, local or just visiting, you’ll find plenty to explore and experience here. Festivals can be found in almost every area of the Caribbean, but some of the most famous and most fascinating are the Trinidad and Tobago Carnival, Pirates Week, and the New Year’s celebration that is Junkanoo. Wherever you come from, you’ll be delighted by the diversity and history on display during these festivals.

Trinidad & Tobago Carnival

Carnival events can be found throughout the world; from London to Miami, people come together on the Monday and Tuesday before Ash Wednesday in order to celebrate. Originally a Catholic religious festival, Carnival - with its masks and masquerades, parades and feasting - has now been adopted by people from all walks of life, regardless of their religious background. In Trinidad and Tobago, Carnival is the most important celebrations of the cultural year, and has been the birthplace and proving ground of some of the islands’ most important musical styles and cultural contributions. Calypso music, for example, was developed at the Trinidad and Tobago Carnivals of the 17th century, while steelpan and - more recently - soca music have also made appearances at the festivities.

Carnival-related events stretch out long before Carnival itself, with must-see tickets like Panorama (testing the skill of steelbands) and the Kings and Queens Costume Competition (with bandleaders in extravagant costumes which can weigh up to 200 pounds) drawing crowds in the thousands. However, Carnival itself begins with the eerie and beautiful J'Ouvert party: at 4am on Monday morning, revellers cover themselves in mud, oil, chocolate, and paint, then dance through the streets to the sound of soca music.

What most people consider “Carnival” starts with Carnival Monday’s riot of colorful costumes and high-decibel soca music, the streets filling with dancers, “Pretty Mas” bands, and food vendors. The next day, things are at a fever pitch, with extravagantly costumed bands waiting to be judged, hyped-up masqueraders in beautiful masks and costumes, and endless parties and events to attend. The dazzling sight of revellers at the Trinidad & Tobago Carnival is one of the world’s greatest treasures, and it makes for a trip you won’t ever forget.

Pirates Week

If you’re looking for a family-friendly festival which will delight both the young and old, Pirates Week in the Cayman Islands is a must-see event. Held for eleven days in November, the festivities here are diverse and fascinating, with a strong basis in history and sense of fun and celebration which takes over the islands for as long as the festival lasts.

Founded in 1977 to liven up the sometimes dreary month of November, the festival celebrates the history of the Cayman Islands through music, dancing, sports events, costume contests, and much more. Whole streets are shut down for parades and parties, stupendous firework displays make the skies over the islands light up in brilliant peacock colors, and there are parties, games, and delicious food everywhere you turn. Things start off with a “pirate landing” at George Town Harbor, where pirate ships provide the backdrop to pageants, live music, and dancing competitions. From then on, it’s a free-for-all, with events popping up in all corners. Many districts are awarded their own “heritage day” to celebrate the unique history of the area, while food festivals, marathons, and child-friendly events like treasure hunts and model boat races ensure that nobody ever has a moment to spare.

At the end of the festivities, the pirates are ceremonially sentenced, which is followed by street dancing, an absolute feast of excellent food, and a fireworks display which will remain in your thoughts for years to come. Pirates Week may not be as well-known as some of the other Caribbean festivals, but there’s no question that it’s one of the most fun.


Imagine spending your Christmas and New Years holidays cruising the Bahamas: palm trees, clear waters, and a sense of peace and joy which befits the holiday season. Yet if you venture into the towns on Boxing Day or New Year’s Day, you’ll be astonished by the sight of costumed parades snaking through the streets, which are filled with revellers and dancers. There are Junkanoo events and parades throughout the Bahamas, but the best place to experience this 400 year old tradition is in Nassau, where dance groups of up to 1,000 people perform in colourful masquerade costumes to the delight of the celebrating crowds.

The best of the Junkanoo dancers are up for prizes and coveted recognition, so the best and brightest of the islands are all in top form and ready to show off their skills in front of the adoring audiences. Performers practice for months for this moment, while costume creation can take just as long, but there are events for everyone to strut their stuff, including a “children’s rush” for the little ones. With both excited locals and visitors from across the world scrambling to find their spot to watch from, there’s a constant atmosphere of delight and surprise which is pulled along by the sound of drumming and laughter.

If you’ve ever thought about spending your winter holidays somewhere tropical, the Bahamas can’t be beat - and if you go, it would be a crime to miss the Junkanoo festivities. Let your hair down, let the rhythm of the drumming get into your bones, and get ready to have the time of your life here in the Caribbean.

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