Caribbean festivals seem to last for days. A few weeks later, another starts. With each island sticking to this haphazard schedule, you are likely to find a festival no matter when you decide to visit. Most famous for their Caribbean music festivals, each island has also has a different style of music to lionize, giving every island a platform to distinguish their specific culture.
A discussion of festivals in the Caribbean begins and ends with the pre-Lenten celebration of Carnival. This is one of the biggest parties, not just of the year, but in the world. And each island celebrates for a different period of time – for instance, Curacao begins festivities right after the new year begins. But nowhere is the celebrations more elaborate, the costumes more intense and the partying more joyous than on Trinidad. In February, there is no place better to witness the outpouring that is the most famous of Caribbean festivals. Here the party goes on long past the point where your senses are dulled by sleep deprivation – eventually your surroundings are a mishmash of colors and stimuli, all imbued with the undulating sheen of a hallucination. You cannot escape from it. You can simply be hanging out in one of the tiny town squares, but it doesn't matter - this is the most important of Caribbean festivals. It will find you. The warm air and decadent smells add to the excitement, food and drink is everywhere and people are happy to share. A mask is handy, but not a necessity. Most faces turn into a blur as you reach the end of the second day anyway.
The music festivals in the Caribbean are quite well known too, and for good reason. Jazz festivals are all over the islands in the winter months – in December it's found in Martinique, in January the focus has shifted to Barbados. But the height of Caribbean jazz music isn't reached until early may, when the St. Lucia version comes around. Musicians and fans the world over descend upon the city of Castries to participate in the festivities. Reggae Sumfest comes along in July. Montego Bay attracts even more tourists at this time, as Sumfest is rapidly growing into one of the largest festivals in the Caribbean. Then Dominica takes center stage with its World Creole Music Festival.
Sailing festivals spread themselves across the calendar too. The Grenada sailing festival opens up the year in late January, and before you know it, it's time for the wildly popular Heinekin Regatta on St. Maarten. But this is just the beginning of the sailing holidays – the Easter Regatta, Easterval Regatta, Rolex Cup Regatta and Antigua Sailing Week all follow close behind. The summer months find enthusiasm for such displays waning. But Pirates Week in the Caymans is a 10 day extravaganza that tries its best to be Carnival in October. It fails, but where else will you find such a heartfelt and festive celebration of all things pirate? Those with real peg legs and eye patches finally get their chance to shine – if you plan on attending, prepare to hear thousands of people overuse the word “y'arr.”
