Must-Attend Caribbean Events Each Month

Caribbean culture is a rich tapestry woven with influences from Africa, Europe, indigenous peoples, and even Asia. Each month in the Caribbean, you’ll find celebrations that welcome visitors to experience the warmth and diversity of the islands. Whenever your schedule allows you to venture down to the islands, good times will await.

January

From Junkanoo in the Bahamas to the Three Kings Festival in Puerto Rico, January is the month to chase away the winter chill with a taste of Carnival and a farewell to Christmas.

February

February is the height of Carnival season in the Caribbean, particularly in Trinidad and Tobago, a celebration that everyone should experience at least once. Moreover, there’s nothing more romantic than a trip to the islands on Valentine’s Day.

March

The post-Carnival season of Lent is more solemn in the Caribbean; however, March still lacks fun and interesting events, including island-flavored Easter and St. Patrick’s Day celebrations.

April

April is typically a month filled with concerts and Easter celebrations in the Caribbean, including the annual Tobago Jazz Festival. The start of low-season rates makes travel this month even more appealing.

May

May is a fantastic month to enjoy live music and sailing in the Caribbean. Events include the Grenada Drum Festival, Barbados’ Gospelfest, and Foxy’s Wooden Boat Regatta in the British Virgin Islands.

June

June’s Crop Over festival serves as Barbados’s version of Carnival, while Vincy Mas is celebrated in the Grenadines. In addition, the St. Kitts Music Festival features a vibrant mix of R&B, hip-hop, calypso, soca, and more.

July

In July, Jamaican jerk flavored foods take center stage during the annual Portland Jerk Festival, where you can savor mouthwatering jerk chicken, pork, sausage, and more. Notably, Antigua also celebrates its Carnival this month.

August

Cup Match in Bermuda celebrates the game of cricket and highlights the August calendar. Furthermore, Sumfest in Anguilla is a vibrant celebration of local culture and sailing.

September

September is generally quiet in the Caribbean; nevertheless, notable events such as fishing tournaments in Jamaica continue to attract attention.

October

Octobers in the Caribbean aren’t solely about hurricane parties. In fact, Nevis and St. Lucia host incredible food festivals, while Bermuda showcases renowned musicians at one of the region’s best music festivals. Furthermore, if sailing interests you, don’t miss Bonaire’s legendary regatta.

November

November features one of the Caribbean’s busiest event calendars, including unique festivities like Pirate Week in the Cayman Islands, which involves a lively pirate “invasion,” the Tranquility Jazz Festival in Anguilla, and the Conch Cracking Festival in the Bahamas.

December

Christmas and New Year’s Eve bring a unique island flavor to the Caribbean, featuring events like the annual Bahamas International Film Festival, alongside traditional parang music festivities celebrated in Grenada during December.