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Can’t-Miss Caribbean Celebrations

From the popular “Carnival” to a celebration of all things pirate, the Caribbean can wow you with festivities all year round.

Even though this year is different, we’re all looking forward to a little celebrating as the holidays approach. While things will certainly be quieter this time, there’s plenty of celebrations that will keep on rolling for years to come, and the Carribean knows how to take festivities to a whole new level!

Here’s a look at five lively celebrations where the parties don’t stop. Add them to your travel bucket list! 

Carnival, Trinidad, St. Lucia, Grenada

There’s a good reason we started with Carnival as one of the most important celebrations. It’s billed as the largest street party on earth! Carnival originated in Trinidad & Tobago and is known for extravagant parades and dancers in brightly colored costumes, feathers, headdresses, and sequins. Calypso music comes from Trinidad, and you can hear it blaring all throughout the parties, or “fetes”, along with its faster, upbeat offshoot, soca. Carnival is officially a two-day festival, starting with a “J’Ouvert” parade at 4 A.M., but Trinidadians begin prepping for Carnival months in advance.

Carnival is also celebrated in St. Lucia, with steel pan competitions and an international soca music battle of bands. A winner is crowned as “monarch” for both the “power” and “groovy” styles.

And in Grenada, famous for its spices, Carnival is referred to as “Spicemas”. The celebration features masked stilt walkers with ties to African folklore that dance throughout the parades.

When it happens: Monday and Tuesday before Ash Wednesday

There’s plenty of riches to discover during Pirates Week.

Pirates Week, Cayman Islands

Did you know the notorious pirate Blackbeard sailed throughout the waters of the Cayman Islands? It’s even rumored that some of his treasure is still hidden on Cayman Brac. While many Caribbean islands have pirate history, none celebrate it quite like the Cayman Islands. This week-long fest has run for more than 40 years and hops from Little Cayman to Grand Cayman and is packed with pirate-themed parties—on land and at sea—treasure hunts, live music and DJs, and even flotillas and fireworks. Yarrr gonna love it!

When it happens: October and November, depending on the island

Brightly colored feathers are everywhere at the celebration!

Junkanoo, The Bahamas

It’s hard to find a livelier street parade than Junkanoo. While the exact origins are unknown, many believe it’s named for “John Canoe” a West African tribal chief. However it started, it’s celebrated today throughout the Bahamas with the largest parade in the capital, Nassau. Junkanoo features dance troupes—of up to 1,000—and colorful costumes like Carnival, but also intricate masks. It even has its own music genre with horns, cowbells and whistles, and drums playing traditional African rhythms. There’s often prize money for best costume, dancing, and music group. And the competition is fierce!

When it happens: Boxing Day, December 26th and New Year’s Day

San Juan’s colorful streets will swell with partygoers during the celebrations.

Saint Sebastian Street Festival, Puerto Rico

This street fest takes place in the historic Old San Juan and was originally created by a priest to celebrate the saint and raise money for his church. Today, it has turned into a much larger fiesta boasting streets lined with artisans selling their wares, lively salsa and bomba music, and choreographed dancing. A unique sight: revelers leading the procession wear larger-than-life paper mache heads, called “cabezudos”, that represent characters from Puerto Rican history and folklore. 

When it happens: January 20

Crop Over, Barbados

There are countless reasons for people to celebrate, but completing the hard work of a harvest is a common one worldwide. In Barbados, Crop Over celebrates the end of the sugar cane harvest. It dates back to the 1600s and rolls on for two whole months!
Featuring sequined costumes, street dancing, and parades, you can hear calypso music coming from tents everywhere as part of the musical competition. Celebrities are even known to join the fun, sporting giant ruffled feathers for the final, blowout parade, called “Kadooment day”.

When it happens: From June 1st to the first Monday in August