Winter 2023 Caribbean Calendar of Events

‘Tis the season to cruise south for the winter! Follow the lead of migrating whales you might be lucky enough to spot, and experience all the Caribbean has to offer on and off the water. Carnival is in full swing all winter in almost every nation in the Caribbean. We highlighted a few, each with its own local cultural spin. You’ll find something for everyone below, from music festivals and foodie events to regattas and horse races.

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ONGOING EVENTS

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Whale Watching in Turks and Caicos

Turks and Caicos

January-February

As humpback whales migrate to their winter breeding ground in the Dominican Republic, the waters of Turks and Caicos are the perfect place to catch a glimpse. Join a whale watching tour, where you cruise to the Columbus Passage for the best views.

Where to Dock: Blue Haven Marina

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CARNIVAL

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Aruba Carnival

Aruba

January 7-February 19

Aruba Carnival kicks off in November, but most events and parades happen in the winter. Travel to Oranjestad for the opening torch parade on January 7 and the lighting parade on February 11, dubbed “Aruba’s favorite evening carnival parade.” Enjoy extravagant costumes, electrifying jump-ups and children’s parades, all culminating in the Burning of King Momo at the end of the season.

Where to Dock: Veradero Arbua Marina & Boatyard

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Trinidad Carnival

Port of Spain, Trinidad and Tobago

February 16-22

The highlights of Trinidad and Tobago’s Carnival lead up to Ash Wednesday. Carnival Monday opens with J’ouvert in the wee hours, and for the next two days, masqueraders dance through the streets in vibrant costumes and body paint to the sounds of calypso. Nodding to their French Creole roots, performers and attendees celebrate Mardi Gras on Carnival Tuesday.

Where to Dock: CrewsInn Hotel & Yachting Center

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Curaçao Carnival

Willemstad Through

February 22

The southern Caribbean island of Curaçao offers an opportunity to experience Carnival starting in the new year. Visitors can expect music festivals with local tumba music and calypso, as well as several parades. Two popular ones are the “Gran Marcha” Parade and Grand Farewell Carnival Parade. While you’re there, explore the island’s secluded beaches, national parks and historical art and architecture.

Where to Dock: Seru Boca Marina

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JANUARY

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Cayman Cookout

George Town, Cayman Islands

January 9-15

The Cayman Cookout is back for the first time since 2020! Come see the world’s most talented chefs and wine and spirits experts at the Grand Cayman Ritz-Carlton for a week of curated culinary events. Foodies relish in top-notch global cuisine, explorers join events across the island, and beverage enthusiasts are in for a treat as the cookout expands its mixology offerings this year.

Where to Dock: The Barcadere Marina

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Fiestas de la Calle San Sebastián

Old San Juan, Puerto Rico

January 19-22

Puerto Rico’s largest festival consumes the streets of Old San Juan with live music, dancing and parades. People wearing huge papier-mâché heads of folk characters are the stars of the show. Look forward to local artisans each day and lively concerts and parties every night.

Where to Dock: San Juan Bay Marina

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Rebel Salute

St. Ann, Jamaica

January 20-21

For almost three decades, this family-friendly music festival has brought reggae lovers together to experience the tunes of local and international roots reggae artists. From dusk ‘til dawn, artists perform while food vendors serve local flavors and artisans display indigenous jewelry and craft items in an arts village. Adult attendees are welcome to partake in and learn about cannabis from renowned experts in the “Herb Curb.”

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Pineapple Cup, Montego Bay Race

Montego Bay, Jamaica

January 21-28

One of the oldest offshore races on the calendar, this course takes competitors from Miami to Cuba through the Northwest Providence Channel, then down a sleigh ride toward the finish line at Montego Bay. Competitors enjoy free dockage and other perks at the Montego Bay Yacht Club, and spectators can join celebratory events.

Where to Dock: Montego Bay Yacht Club

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Bequia Music Festival

Bequia, St. Vincent and the Grenadines

January 25-29

Dock at the second largest island in the Grenadines, known as a mecca to the Caribbean cruising yacht community, for an unforgettable mash-up of musicians. Most artists come from elsewhere in the Caribbean, making for an intimate festival with diverse tunes. When you’re not grooving, explore the lush green hills and white sand beaches of Bequia.

Where to Dock: Bequia Marina

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Grenada Sailing Week

Grenada

January 29-February 3

Chaired by a Grenadian and created by sailing enthusiasts who didn’t want the keelboat regatta to end, this week of racing welcomes contestants from 20+ countries. The first race kicks off at Grenada’s sister island Carriacou and ends in Grenada, and the second set takes place in Grenada. Spectators can look forward to performances from talented local bands and plenty of local Mount Gay Rum from Grenada.

Where to Dock: Prickly Bay Marin or Port Louis Marina

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FEBRUARY

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Caribbean Multihull Challenge

St. Maarten

February 3-5

Hosted by the Sint Maarten Yacht Club, this race takes contestants through Anguilla and French St. Martin and ends in Dutch St. Maarten. Contestants sail catamarans and tri-hulls — new and classic — through this scenic route. Everyone else enjoys events at the club or joins the non-competitive Cruising Multihull Rally. Participants cruise to Anguilla for beach games, fine dining and a beach bar on Day 1, and Anse Marcel for more dining and partying on Day 2.

Where to Dock: Sint Maarten Yacht Club (private) or Palapa Marina (transient)

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Valentine’s Day Jump Up

Christiansted, St. Croix, U.S. Virgin Islands

February 17

Boaters cruising the Caribbean won’t want to miss the Valentine’s Day rendition of this Carnival-esque celebration. Steel drummers and other musicians, local food vendors, and artisans fill the Christiansted streets and boardwalk in the evening. The most iconic part is when Moko Jumbies, a Virgin Islands tradition said to ward off evil, dance in the streets in their eccentric costumes.

Where to Dock: Green Cay Marina at Tamarind Reef Resort

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BVI Wreck Week

British Virgin Islands

February 12-18

Cruise to the British Virgin Islands to celebrate maritime treasures, underwater wrecks and art reefs. Divers get to explore the wrecks with local operators, but events galore are held for landlubbers. Locals share tales of Blackbeard’s time in BVI, and the local boat-building history (Tortola Sloops was created here), alongside welcome and farewell parties on the beach.

Where to Dock: Nanny Cay Resort & Marina

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Dominican Independence Day

Samaná, Dominican Republic

February 27

Celebrate Dominican Republic’s independence from Haiti in 1844 in this picturesque beach town on Samaná Bay. Parades and parties run along the Malecón promenade and its businesses. Nature lovers are fascinated by the local Whale Museum and views of humpback whales, who come to the Bay for mating seasons. Those seeking relaxation should cruise to Cayo Levantado, a tiny island with gorgeous beaches.

Where to Dock: Ocean World Marina

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MARCH

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Sandy Lane Barbados Gold Cup

Garrison Savannah, Barbados

March 4

Make your way to Garrison Savannah, the home of horse racing in Barbados, for one of the most prestigious events in the Eastern Caribbean equestrian scene. Top local, regional and international jockeys race on a 1,800 meter turf course. And no trip to Barbados is complete without a rum factory tour at the Mount Gay Vistors Centre!

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Superyacht Challenge Antigua

Antigua & Barbuda

March 6-11

Boaters have a blast watching a small, exclusive fleet of spectacular superyachts race 12-30 mile courses along the stunning south coast of Antigua for five days. Only 12-15 yachts in excess of 80 feet are expected to enter and enjoy the amenities at Nelson’s Dockyard. Owners, guests and crew enjoy exploring the fleet and partaking in laid back social events. superyachtchallengeantigua.com

Where to Dock: Nelson’s Dockyard Marina

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Moonsplash

Anguilla

March 10-12

Avid concert goers won’t want to miss the oldest independent music festival in the Caribbean under the stars! Bankie Banx, the reggae artist known as “Anguillan Bob Dylan,” owns the Dune Preserve venue and has performed at the festival himself. Other big names such as John Mayer, Nas, Toots and the Maytals, and Inner Circle have been in previous lineups.

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Corales Puntacana Championship

Punta Cana, Dominican Republic

March 20-26

At this PGA Tour event, golf aficionados can see 120 players compete to earn points for the Fed Ex Cup. The Puntacana Resort & Club, host of the event, boasts an exclusive 18-hole course with natural cliffs and majestic carolina quarries. While here, book a resort on the Coconut Coast, lay out on Punta Cana’s pristine white beaches, or go zip-lining, windsurfing, or sailing.

Where to Dock: Marina Cap Cana

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St. Thomas International Regatta

St. Thomas, U.S. Virgin Islands

March 24-26

Round out your winter in the Caribbean with the “Crown Jewel of Caribbean Racing.” Join the shoreside fun with happy hours, dinners and live music at the St. Thomas Yacht Club every night of the race. History buffs should check out Blackbeard’s Castle and Fort Christian, and all visitors should dip into St. Thomas’s popular snorkeling spots.

Where to Dock: St. Thomas Yacht Club (private) or Sapphire Beach Marina (transient)