8 Great Nautical Ways to Celebrate the Holidays in the Caribbean

Trade a sleigh for sea spray and cruise the Caribbean for the holidays. Many islands host nautically-themed celebrations in December and early January. Here is a sampling of festive shindigs not to miss!

DECEMBER 8
Christmas Hamper Race, Trinidad.
The Trinidad & Tobago Sailing Association hosts this cherished year-end tradition. The race starts at Noon out of Hart’s Cut, Chaguaramas, and is open to both keelboat and dinghy racers. “This exciting event promises fun on the water, as every participating boat receives a festive hamper filled with a variety of goodies, including drinks, food, and sailing gear, generously donated by our supportive partners,” says Michelle Kong, general manager of the Trinidad & Tobago Yachting Association. Last year, over 30 boats, including Optimists, C420s, Lasers, MR15s, and keelboats, turned out, with Laser racer Abigail Affoo taking home the win. Those looking for an excellent holiday gift will find it in the newly released book, ‘We Come to Sail: The Trinidad and Tobago Sailing Association Story.’ The book is available for purchase from the TTSA’s office in Chaguaramas and at Peake Trading Limited. www.ttsailing.org 

DECEMBER 14
San Juan Christmas Boat Parade, Puerto Rico.
Held annually on the second Saturday of December, or this year, December 14th, this nautical parade is as fun to watch as it is to participate. Dozens of sport fishers, power yachts, and sailboats ablaze with lights, ornaments, and crews clad in red and white Christmas costumes fill Bahia Urbana in Old San Juan with seasonal cheer from 6 to 8 p.m. There’s music, too! More than one sportfisher has hosted a live band using the cockpit as a stage. Want to join? Call (787) 722-0177 for more information. The best spectating spots are along the Bahia Urbana, the Old San Juan waterfront from Piers 1 to 4, the Catano waterfront, and the Pan-American Pier. Afterward, stroll through the streets of Old San Juan to look at the Christmas Lights, finishing by stopping at a calle-side bar for the island’s unofficial holiday drink – a coquito, akin to eggnog spiked with rum. clubnauticodesanjuan.com/V2/xmas-boat-parade/

DECEMBER 15
Christmas Tree Lighting
DECEMBER 31
New Year’s Eve Celebration & Fireworks, Nelson’s Dockyard, Antigua.
“The enchanting Nelson’s Dockyard invites everyone to celebrate a tapestry of old, new, and emerging traditions at this annual tree lighting,” invites Vaughan Skerritt, writer and director of advertising strategy for the Antigua and Barbuda Department of Culture. “This cherished event, themed this year ‘A Cultural Christmas,’ showcases the vibrant fixtures, delectable foods, and melodic sounds that have graced our holiday seasons for generations, wrapping everyone in a warm embrace of nostalgia.” Those in Antigua at the end of the month can take part in the New Year’s Eve celebration at the Cooper and Lumber Store Hotel. “The excitement doesn’t end there!” says Skerritt. “Embrace a delightful new tradition at The Block House, the perfect spot to witness at least five dazzling fireworks displays at midnight. Gather your loved ones and experience the moment’s magic—arrive early, as this secret is spreading fast!” www.facebook.com/nelsonsdockyardnationalpark 

DECEMBER 16
Christmas Concert & Visit from Santa Claus, Marina Casa de Campo, Dominican Republic.
All guests from the marina, hotel, and villas in Casa de Campo are invited to this annual holiday happening that takes place in Plaza Portofino, says Virma Nunez, marketing manager for Marina Casa de Campo. “This is a Christmas Carols concert with a visit from Santa, which makes it a family event full of joy and happiness for children and adults alike. It ends with a small concert with Christmas carols and tropical music with a Christmas touch.” New in 2024, Casa de Campo is celebrating its 50th anniversary with several activities through the end of the year, culminating with its New Year’s Eve Party. www.marinacasadecampo.com.do 

DECEMBER 30
New Year’s Eve Sail Boats Parade, St. Barth’s, French West Indies.
Join a three-decade-plus tradition and join the parade around the 8.1 square-mile island of St. Barth’s. The St. Barth’s Yacht Club hosts this charity event, which features a fun pursuit-style circumnavigation from 10 a.m. to 4 p.m. and beachside Awards afterward. “It’s open to any boat longer than 24 feet. The registration is 6$/foot. All the profit goes to the sailing program of the St Barth’s Yacht Club,” says Berenice Diveu, club manager. “Last year, Look Up, a Diam 24 won, and in the past, Phaedo 3, Win Win, Symmetry, and Maelia won the event. This year’s new and major change is that the event will happen on the 30th of December, so all the boats and crews can easily enjoy their New Year’s Eve.” There will be a Skipper’s Briefing and Cocktails at the Club on December 29, from 6-8 p.m. www.stbarthyachtclub.com 

DECEMBER 31
Foxy’s Old Year’s Night Party, British Virgin Islands.
All waterways in the Virgin Islands lead to the BVI’s Great Harbor on Jost Van Dyke to ring out the old year and into the new. Foxy’s Tamarind Bar has ranked one of the top places in the world to spend this holiday for celebrities and everyday folks alike. There are so many boats in Great Harbor by the time the fireworks go off at midnight that it feels like you can walk on water from one to another with the dazzlers lighting the way. This year’s party theme at Foxy’s is the Mad Hatters Tea Party, so dress the part. The night features a special menu and all local live bands from the Virgin Islands. foxysbar.com 

JANUARY 1, 2025
SSCA Potluck-Style GAM, Trinidad.
The 30-plus-year tradition continues, with Jesse James, owner of ‘Members Only’ Maxi Taxi Service, and his wife, Sharon Rose, hosting this cruiser’s get-together for the past 27 years. “I also invite members from the Ocean Cruising Club, Seven Seas Cruising Association, and all cruisers who are in Trinidad to see the New Year usher in. Everyone brings a dish to share, and I sponsor the Trini-style BBQ chicken for everyone. Drinks are also donated by the business community, as are many door prizes. It’s an international community made up of cruisers worldwide,” says James, who was awarded the Seven Seas Cruisers Association ‘Camaraderie Award’ and the Seven Seas South Bound II Award. The event takes place at the Wheel House Pub, Tropical Marina, in Chaguaramas, from Noon-3 p.m. www.jessejamesmembersonly.com 

JANUARY 5, 2025
Fuik Day (Fuikdag), Curaçao.
Start the New Year off on the water with Curaçao’s biggest yearly boat party. What started as a small party with friends on three boats in the 1960s is now a yearly nautical celebration. The name Fuikdag comes from the name of the bay, Fuik, on the southwest shores of the island. Anyone with a boat can join. Or buy a ticket on boats selling spots to the party. The festivities include food, drink and live DJs with singing and dancing. www.curacao.com  

Carol Bareuther has written for ALL AT SEA since 2004.