Caribbean Calendar of Events Winter 2024


From traditional parades to music festivals and sailing regattas, the Caribbean boasts an array of events showcasing the cultural diversity within each country. To escape the cold, head south this season to feast on homemade regional dishes, watch watercraft race across tropical waters, dance to culture-infused music and enjoy all the islands have to offer. Check out the following events hosted from January to March.


Island Exodus

Runaway Bay, Jamaica, January 14 – 18

Kick off the new year with an intimate concert experience at the coastal town of Runaway Bay. Taking place at Jewel Paradise Cove Resort Jamaica, guests can purchase all- inclusive resort packages and enjoy four days of live music on the beach. The stellar lineup announces the return of rock band Gov’t Mule, plus a solo act from Warren Haynes.

Rebel Salute | Credit:

Fiestas de la Calle San Sebastián (San Sebastián Street Festival)

Old San Juan, Puerto Rico, January 18 – 21

This annual tradition honoring Puerto Rican heritage is the country’s largest celebration. Enjoy a day-long festival with vendors, live music, authentic cuisine and parades showcasing captivating performances and intricate costume designs.

Where to Dock: San Juan Bay Marina

Rebel Salute

Priory, St. Ann, Jamaica, January 19 – 20

For more than two decades, this festival has honored traditions celebrating healthy living and the preservation of authentic roots reggae. The venue is located on the north coast of Jamaica overlooking the Caribbean Sea and hosts various artists and vendors selling indigenous jewelry, clothes and crafts. For the full experience, stay overnight at the campground onsite.


Hope Town Music & Rum Festival

Abaco, Bahamas, February 6 – 11

Situated along the gorgeous shores of Elbow Cay, this decade-long tradition hosts beachfront concerts and vendors to honor the Hope Town community and its resilience from past hurricane damage. Catch events hosted at local resorts with a variety of tastings from local and international rum distillers.

Where to Dock: Hope Town Inn & Marina

Dominican Republic Carnival | Credit: Larry Penaloza from Pexels

Union Island Conch Festival

Saint Vincent & the Grenadines, February 23 – 25

Celebrate the significance of Union Island’s conch industry at this traditional food competition and fun fest. Feast on conch water, stew, salads, curry, chowder and pasta as chefs create delicious masterpieces. Competitions include conch and dumpling eating, conch shell blowing, conch chopping and kayaking.

Where to Dock: Anchorage Yacht Club

Dominican Republic Independence Day

Dominican Republic, February 27

This month is an exciting time to be in the DR as both Carnival season and the country’s Independence Day take place in February. Since its liberation from Haiti in 1844, this has been honored as one of the country’s most important cultural holidays. Enjoy parades, music, delicious food and festive traditions.

Where to Dock: Ocean World Marina


Virgin Islands Jam Fest

St. John, USVI, March 7 – 9

Overlooking waters of the U.S. Virgin Islands, kick back, relax and watch grassroots music concerts at this quaint and cozy venue that usually hosts about 350 people. The 2024 lineup includes Blac Rabbit, Kyle Smith and Patsy & The Heavy Set, to name a few.

Where to Dock: St. John Marina

SXM Festival

Atlantis Paradise Island Resort | Credit: Astro Aerials

Saint Martin, March 11 – 18

This plush event hosts a seven-day electronic music festival throughout unique venues across the island. Dance from sunrise to sunset in beach clubs, lush rainforests, stunning villas, secluded beaches and aboard luxury yachts. Embark on watersports, ziplines and catamaran charters.

Where to Dock: Marina Fort-Louis

Atlantis Wine & Food Festival

Nassau, Paradise Island, Bahamas, March 13 – 17

Set your tastebuds on spectacular cuisine this season at the Atlantis Paradise Island resort. Renowned chefs and culinary personalities will showcase their best dishes, wines and spirits at this five-day festival. Events kick off with Wine Down Wednesday presenting stunning views of Nassau Harbor and the exclusive Swirl Party offering unlimited food and wine at the Golf Course Club House.

Where to Dock: Atlantis Marina

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