From joyous street parties to celebrations of food and culture, find your fiesta with our guide to the travel season’s top Caribbean festivals.
PHOTO: JAMAICA FOOD & DRINK FESTIVAL.
Jamaica Food & Drink Festival – November 7 to 10, KINGSTON, JAMAICA
Some of Jamaica’s best chefs and wine and spirits experts will come together for the 10th annual celebration of the island’s rich food and drink culture. There are several marquee pre-festival events: If you’re in Kingston on October 8, don’t miss Saveur, the multi-course, wine-paired tasting menu at Broken Plate, a rooftop restaurant where chef Damion Stewart serves up inventive, locally inspired dishes like oxtail wonton and curried goat pasta. During the festival dates in November, visitors can experience a buzzing craft market in downtown Kingston and an intimate meal at the Jamaica Food and Drink Kitchen prepared by José Mendín from Miami’s Pubbelly Sushi and Mathieu Masson-Duceppe of Cooking Channel’s Fire Masters.
PHOTO: ANTIGUA AND BARBUDA TOURISM AUTHORITY.
Antigua and Barbuda Art Week, November 27 to December 3, PRIMARILY ST. JOHN’S, ANTIGUA, BUT ALSO ON BARBUDA
As if Antigua’s 365 beaches weren’t picturesque enough, the second annual Antigua and Barbuda Art Week celebrates the country’s visual arts, fashion, music, film and dance scenes. This year’s edition will feature an exhibition of local artists’ work, as well as performances, artist showcases, screenings, art walks, studio tours and community events on both islands: During last year’s Art Hop, visitors met three artists working in studios near Barbuda’s stunning Codrington Lagoon. The festival also hosts an artist-led Paint, Sip & Eat event, where you can grab a brush and create your own work of art inspired by the islands’ lush landscapes.
PHOTO: ANTIGUA AND BARBUDA TOURISM AUTHORITY.
As if Antigua’s 365 beaches weren’t picturesque enough, the second annual Antigua and Barbuda Art Week celebrates the country’s visual arts, fashion, music, film and dance scenes. This year’s edition will feature an exhibition of local artists’ work, as well as performances, artist showcases, screenings, art walks, studio tours and community events on both islands: During last year’s Art Hop, visitors met three artists working in studios near Barbuda’s stunning Codrington Lagoon. The festival also hosts an artist-led Paint, Sip & Eat event, where you can grab a brush and create your own work of art inspired by the islands’ lush landscapes.
PHOTO: COURTESY OF SUGAR MAS.
Sugar Mas (Saint Kitts and Nevis National Carnival), December 13, 2024, to January 2, 2025, BASSETERRE, SAINT KITTS AND NEVIS
The first epic Carnival of 2025 officially kicks off this December, and you can catch pre-Carnival events, like musical competitions, even earlier. Sugar Mas offers the inimitable music and artistry that experienced revelers expect of any Caribbean Carnival: steel pan drums, soca fêtes and parades of intricately costumed masqueraders. Here, Carnival also celebrates local artisans — find last-minute gifts like perfumes, clothing and masquerade-friendly accessories at the Midnight Escape Street Festival, held on Christmas Eve. Sugar Mas runs right into the New Year, making the dual-island nation of Saint Kitts and Nevis the perfect place to ring in 2025.
PHOTO: DISCOVER PUERTO RICO
Fiestas de la Calle San Sebastián, January 16 to 19, 2025, OLD SAN JUAN, PUERTO RICO
Held the third weekend of January, the San Sebastián Street Festival closes out la Navidad, the country’s extended Christmas season. Known as “la SanSe,” Old San Juan’s beloved cultural celebration (and the island’s largest festival) is mostly celebrated in the streets: Nearly half a million locals and visitors gather for the parades, dancing and live bomba, plena and salsa music. There’s also a street market and Puerto Rican street food like empanadillas, bacalaitos and tostones, plus concerts and parties that ensure the festivities continue long after sundown.
PHOTO: HOLGER WOIZICK/UNSPLASH
Trinidad and Tobago Carnival, February 25 to March 5, 2025, PORT OF SPAIN, TRINIDAD AND TOBAGO
Dubbed “The Greatest Show on Earth,” Trinidad and Tobago Carnival brings droves of costumed revelers together to play mas (masquerade) in a tradition that calls back to the islands’ resistance to slavery. These are some of the biggest fêtes, most elaborate costumes and most joyfully strenuous activities of any Caribbean Carnival. Expect all-day parties like Soca Brainwash and gatherings like J’ouvert (French for “daybreak”), which kicks off the two official days of Carnival processions with a pre-dawn, paint-soaked street celebration. Warm-up events include the Soaka Arts & Music Festival, where you can watch steel pan bands compete or dance at an all-night soca party.
PHOTO: LAURENS MOREL
St. Maarten Heineken Regatta, March 6 to 9, 2025, SIMPSON BAY, SINT MAARTEN
The 45th edition of this renowned regatta is expected to attract more than 20,000 visitors, and it’s easy to see why the event is so popular: Sint Maarten’s beautifully clear, warm waters and cooling northeast trade winds make for optimal race conditions. If you’re not competing, watch the action from the official Spectator Boat, which offers breakfast, lunch and an open bar. There’s more fun to be had on dry land: Regatta Village, hosted at Port de Plaisance Resort, turns into a nightly music festival featuring some of the Caribbean’s top artists (reggae legends Kevin Lyttle, Rupee and Tarrus
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Disclaimer: Current travel rules and restrictions can change without notice. The decision to travel is ultimately your responsibility. Contact your consulate and/or local authorities to confirm your nationality’s entry and/or any changes to travel requirements before travelling.
