As U.S. temperatures drop and international travel restrictions do the same, it’s time to cruise through the Caribbean’s azure waters to get a culinary and cultural taste of the islands. Whether you’re a foodie, history buff or racing enthusiast, the islands have something for you. Read on to learn about all the cultural, historical, sports, food, drink and music celebrations that Caribbean countries offer boaters this winter.
Majority Rule Day
Declared a public holiday in 2014, Majority Rule Day commemorates the day in 1967 when black Bahamians gained majority rule and won their first national election. Bahamians everywhere take the day to celebrate and “remember the long struggle for human dignity, equality and social justice,” as Prime Minister Minnis put it. While triumphant events happen across the islands, Freeport is known for its parade, and George Street in the capital city of Nassau is home to events and keynote speeches.
Fiestas de la Calle San Sebastián
Old San Juan, Puerto Rico
Puerto Rico’s largest festival, dedicated to the Catholics’ St. Sebastián and local community, consumes the streets of Old San Juan with live music, dancing and parades. The inaugural parade on San Sebastián Street highlights Cabezudos, a group of people disguised with huge papier-mâché heads representing folk characters. Each day, the city fills with local artisans selling paintings, jewelry and other goods. And each night, the city fills with lively concerts and parties.
Great Exuma Classic & Great Abaco Classic
Sandals Emerald Bay, Great Exuma, The Bahamas
The Abaco Club, Great Abaco, The Bahamas
Golf enthusiasts won’t want to miss these two Korn Ferry Tour tournaments, both located on the water in stunning Bahamian resorts. Explore the 365+ islands or try fly-fishing for bonefish in Great Exuma, and go diving or explore Walker’s Cay National Park in Great Abaco. Don’t forget to check out the Emerald Bay Marina and Abaco Yacht Club while you’re there!
Pineapple Cup, Montego Bay Race
Montego Bay, Jamaica
One of the oldest offshore races on the calendar, the first Pineapple Cup was in 1961. Competitors in this 811 nautical mile race first head from Miami for the Northwest Providence Channel, sail toward the tip of Cuba, and enjoy a 240-mile downwind sleigh ride toward the finish line at Montego Bay. Competitors enjoy free dockage and other perks at the Montego Bay Yacht Club, and spectators join celebratory parties and events.
Betico Croes Day
Experience the island of Aruba as it celebrates Betico Croes, a political activist event credited by obtaining Aruba’s “Status Aparte” within the Dutch Kingdom in 1986. Soak in this historic day and participate in celebratory activities from a Harley Davidson bike tour to culinary festivals.
Aruba Carnival Season
Come get a taste of the Caribbean tradition that is Carnival. This months-long celebration was started by European settlers. Arubans, including former slaves, reclaimed Carnival and made it the cultural phenomenon it is today. Dock in Aruba any day in January and you’re bound to catch a parade of throbbing music, decorated floats and flamboyantly dressed groups dancing in the street.
Bob Marley Week
Reggae fans cruising in the Caribbean this winter won’t want to miss the reggae legend’s birthday celebrations. Falling at the start of Black History Month and ending with Marley’s birthday, this week fills Jamaica’s capital city with events such as concerts, parades and karaoke competitions. While you’re there, make sure to attend events at the Bob Marley Museum, located in Marley’s former home and studio.
Bob Marley Birthday Bash
February (dates TBD)
Continue celebrating the reggae legend’s birthday by cruising over to Negril. The town lights up with reggae and cultural events in February. In between events, soak up the sun at Seven Mile Beach overlooking Long Bay and try the local cuisine at one of many jerk restaurants.
Valentine’s Day Jump Up
Christiansted, St. Croix, U.S. Virgin Islands
This Carnival-like cultural party is held four times a year, and you won’t want to skip the Valentine’s Day rendition. Steel drummers and other musicians, local food vendors, and artisans fill the streets and boardwalk from 6:00 p.m. and on. Mocko Jumbies, a Virgin Islands tradition said to ward off evil, dance in the streets in their eccentric costumes. Sample local cuisine and crafts and soak in USVI culture with your loved one this February.
Jolly Harbour Valentine’s Regatta
St. Mary, Antigua & Barbuda
Dock at the Jolly Harbour Yacht Club in the Antigua resort village of Jolly Harbour. Enjoy the regatta festivities and explore the area in between; there’s something for everyone. Check out the pristine beaches, Jolly Harbour Golf Club or Greencastle Hill National Park, home to volcanic rock formations.
Dominican Carnival Parades
February 6, 13, 20, 27
National Carnival Parade
Every Sunday in February, carnival parades illuminate cities across the Dominican Republic. You’ll recognize some elements from other Caribbean carnivals, but each city reveals its unique folkloric traditions and beliefs with the parades’ costumes, masks and mythical characters. The capital of Santo Domingo rounds out the carnival season with a national parade along the Malecón waterfront boulevard.
Procigar Festival 2022
Santiago, Dominican Republic
Home to some of the most popular cigars and finest tobacco, Santiago has earned its title of Cigar Capital of the World. Tobacco aficionados can register for the festival to enjoy cigar field and factory tours, unreleased cigars, seminars and workshops, and exclusive dinner parties.
Taste of Rum, Rums of Puerto Rico
Old San Juan, Puerto Rico
Responsible for more than 70% of the rum sold in the United States and one of the biggest rum festivals in the world, Puerto Rico has earned its reputation in the industry. After a 2021 hiatus, Taste of Rum is ready to wow attendees with not only local rums, but also live music, rum master classes, local arts and crafts, and food. After the festival, extend your stay to soak in the history, music, cuisine and culture of Old San Juan.
St. Thomas International Rolex Regatta
St. Thomas, U.S. Virgin Islands
Known as the crown jewel of Caribbean racing, this is a must-see for boaters cruising the region. Dock at the hosting St. Thomas Yacht Club and enjoy the shoreside excitement it has to offer. Round out your trip with other excursions on the island: everyone should try snorkeling in St. Thomas, and history buffs will love visiting the Blackbeard’s Castle watchtower.