10 Best Events in the Caribbean: What Not to Miss During Your Caribbean Vacation

Known for its intriguing cultures, vibrant festivals, fun carnivals, stunning forests, soft sands, luscious forests, and luxury resorts, the Caribbean is a dream getaway for many. One great way of experiencing each country’s culture at its finest though, is by attending one of the many festivals and events that take place in the Caribbean annually.

To help you find the best events to attend during your stay, we’ve put together a list of the 10 best events in the Caribbean, so you can discover the best festivals, street parties, and sailing regattas in the region.

Antigua Sailing Week: Antigua

If you’re looking for a more upscale celebration, why not attend one of the world’s most prestigious Yacht racing events?

This regatta takes place in Antigua every year, usually around the end of April / beginning of May, as sailing yachts and boats travel to this small Caribbean island for this week-long event of a series of races around the island.

Cayman’s Pirate Week: The Cayman Islands

Giving ‘The Pirates of the Caribbean’ a whole new meaning is the Pirate Week, taking place across the three Cayman Islands for an entire week every November.

This festival celebrates the history of Pirates with street dances, firework displays, costume contests, parades, and even more for the whole family to enjoy. So if you like drinking rum, dressing like a pirate, and walking the plank, be sure to enjoy Pirate Week as part of your next vacation.

Reggae Sumfest: Jamaica

An amazing fusion of classic Jamaican food, culture, and drinks, Reggae Sumfest is one of the best festivals around for lovers of Jamaica and its music scene. Referred to by many as the Caribbean’s version of Coachella, Reggae Sumfest was created when Reggae Sunsplash (the country’s previous number-one music festival) came to an end in 1991.

Reggae Sumfest brings 6 nights of fun to the Island of Jamaica every year during the month of July and boasts some amazing attractions, such as a white party, a beach party, great music, and plenty to drink. The festival has welcomed performances from a host of names known internationally, such as Shaggy, Sean Paul, Rihanna, Nicki Minaj, Usher, Wiz Khalifa, 50 Cent, and Kanye West, as well as many of the Caribbean’s biggest artists.

Junkanoo: The Bahamas

If you’re visiting the Caribbean over the Christmas period, you’ll want to head on over to the Bahamas for Boxing Day! Taking place just after Christmas, this festival boasts groups in garish costumes that celebrate the Bahamian culture. 

The Junkanoo celebrations began as an aspect of African chattel slavery in British American colonies, and so have roots in West African culture. It dates back to the celebrations of the plantation slaves during their three-day vacation every year, over the Christmas period.

It’s an all-night party though, so instead of heading to bed at the end of Christmas Day, take a short nap, and head out onto the streets between the hours of 1:00 am and 9:00 am on Boxing Day, where you can enjoy Goombay music and heaps of participants hoping to be crowned the Best Junkanoo Group.

Planning on attending the festival Tourists are encouraged to join in, however, you’ll first need to look up the National Junkanoo Association’s rules to ensure you know what to do.

Barbados Crop Over: Barbados

If you’re planning a trip to Barbados between July and August, and are looking to enjoy non-stop dancing, non-stop fun, and non-stop rum, then this party is one for you! Check the annual dates of the Barbados Crop Over, an annual celebration of the sugar crop harvest.

Taking place on the streets of Barbados, this party lasts for a few weeks at a time each year, and travelers can immerse themselves in this fun-filled celebration too. The Barbados Crop Over culminates in a Kadooment Day grand carnival parade, with people dancing in the streets, adorned with bright colors, feathers, sequins, and everything else you might associate with a Caribbean Carnival.

Trinidad and Tobago Carnival: Trinidad and Tobago

Each country in the Caribbean boasts its own unique celebrations, and Trinidad and Tobago is no different. Taking place on the island of Trinidad, parades line the streets during the Monday and Tuesday before Ash Wednesday every year, and this two-day celebration features bright colors, flavorful music, and plenty of dancing and fun!

If you’re looking to witness a truly spectacular Caribbean Carnival, then this is one to be at!

Jamaica’s Rebel Salute: Jamaica

Another one of the Caribbean’s biggest music festivals is, of course, another which takes place in Jamaica and is famously known as Rebel Salute. Celebrating the rich Reggae culture of Jamaica, Rebel Salute was created by Tony Rebel and his team, and for 30 years has captivated audiences by striving to deliver the largest showcase of roots reggae and culturally themed dancehall music festival. 

Rebel Salute takes place in January and is a two-night event where cultural music, fun dancing, and great drinks are to be had. If you’re planning on attending this event, it must be noted that smoking weed is not permitted at the festival, a rare instance in Jamaica.

Junkanoo Festival: Turks & Caicos

Similar to the Junkanoo festival in the Bahamas, the Junkanoo festival of Turks and Caicos has roots in West African culture and dates back to the celebrations of the plantation slaves during their three days off per year.

Celebrated across December and January, this vibrant party features locals in handmade costumes, taking to the streets and often playing traditional ripsaw or rake-and-scrape music. There’s a huge variety of instruments to be seen and plenty of fun to be had.

If you’ll be visiting at a different time of year, however, there is a museum located in downtown Nassau, Providenciales, dedicated to the Junkanoo tradition. During the festival, it is where many of the best celebrations take place.

Spicemas: Grenada, Carriacou, Petite Martinique

Taking place in August across a ten-day period, Grenada, Carriacou, and Petite Martinique all celebrate the intriguing Spicemas Carnival (known as August Mas locally). This Carnival began in the late 1800’s and occurs every year in a medley of calypso and soca beats, and pageantry.

The Sunday grand parade (Dimanche Gras) takes place in the harbor capital of Saint George’s, but one fascinating and unique element of this festival not to be missed is the Monday J’ouvert parade, where traditional Devil Mas bands dance through the streets from their parishes. 

St Lucia Carnival: St Lucia

First taking place just after WWII ended in 1947, the St Lucia Carnival started out as a small group of people banging on glass bottles, dressed in ragged clothing, parading the streets.

Now, the festival takes place annually, as a symbol of freedom and religion, and the opening street party is an event to not be missed if you’re traveling to St Lucia during this event. Tourists are more than encouraged to join in with the festivities.

Partygoers typically wear extravagant, feather-filled headpieces, and dance in the streets to banjos and drums, as well as calypso, reggae, and soca music.

Each year, a Carnival queen is selected to take the crown too!

Which of these amazing events would you like to attend? Let us know in the comments! If you’re planning on visiting the Caribean for a getaway, and need assistance in planning your dream trip, head on over to our Contact Us page, where you can get in touch with one of our trusted travel advisors.

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