As the cooler days of fall approach, we look to the Caribbean for an inspired getaway. The islands come alive with a myriad of vibrant cultural festivals, offering the perfect excuse to extend your summer while experiencing the region from an entirely new perspective. 

Here are a few of the upcoming regattas, festivals, and must-see events we’re most excited about this season.

Columbus Day Regatta

October 10 – 11 | St. Thomas

The atmosphere at the start of a boat race in the Caribbean is unlike any other. Locals and visitors come out to support their favorite crafts, either standing on shore or celebrating on their own boats, and there is a noticeable energy in the air. A favorite race weekend in St. Thomas is the Columbus Day Regatta, a gathering in Cowpet Bay that draws competitors from around the world. There are all types of races from dinghy to big boat racing each day, and throughout the weekend, the island is alive with related celebrations.

Latin Festival

October 17 – 23 | Nevis

A week-long festival of fiery dance competitions, live music, Latin and Caribbean flavors, and cultural expression is coming to Nevis this October. The Latin Festival first began in an effort to create an interchange of cultures between people of different nationalities, and today it stays true to that mission with festivities inspired by and performed by people from Caribbean and Latin American countries. Visitors can expect dance and art workshops, a Latin Caribbean movie presentation, fireworks show, and more. 

Antigua & Barbuda Independence Week

October 23 – November 1 | Antigua

Independence celebrations in the Caribbean always present a wonderful opportunity to experience the culture of the islands through community parades, local food fairs, and music. During the 35th annual Antigua & Barbuda Independence Week, the celebration will see the island decked in yellow and red—the national colors—with everything from car racing to fashion shows happening throughout the week. Be sure to observe some of the historic events such as National Dress Day amidst the lively festivities.

St. Barth Gourmet Festival 

November 3 – 6 | St. Barth

Held each fall on the food-centric island of St. Barth, the St. Barth Gourmet Festival is an international food festival that attracts world-renowned chefs, including patron chef Christian Le Squer of the Four Seasons Georges V Hotel in Paris, for four days of professional competitions and dining events. Some of the island’s best chefs join the guest chefs in a celebration of gourmet French cuisine. There will be special menus with wine pairings, a mixology competition for barmen, and local restaurants offering delectable French dishes. The event is one of the Caribbean’s most popular annual showcases, so make your reservations now.

Livin in the Sun Music Festival

November 11 – 13 | Anguilla

Photo: Sandy Island

Visitors who enjoy the eclectic, lively music of the Caribbean will want to attend the Livin In the Sun Music Festival in Anguilla this fall. The three-day fest invites DJs from all over the world along with local talent for a celebration of island life and living carefree in the sun. There’s just enough time to rest in between the full lineup of events, with daytime happenings taking place from 10 a.m. to 4 p.m. on Sandy Island and after dark events taking place from 10 p.m. to 4 a.m. in various local hotspots.

Jolly Harbor Yacht Club Annual Regatta

November 20 – 22 (2015 dates) | Antigua

Beginners and experienced boaters alike will enjoy the Jolly Harbor Yacht Club Annual Regatta, a fast-paced weekend of racing and local entertainment that draws hundreds of visitors to the island of Antigua each year. Take to the seas, even if you are a novice racer, or choose to spectate from shore. There will be an array of live music performances and celebrations across the island following the races on Saturday and Sunday as well as an awards ceremony at the end of the regatta.

St. Kitts and Nevis National Carnival

End of December | St. Kitts and Nevis

The majority of Carnival celebrations take place during spring, but fall visitors to the Caribbean will want to attend the St. Kitts and Nevis National Carnival, which blends the spirit of Christmas with the vibrant display of Caribbean culture and African heritage. Soca music plays throughout the cities, the J’ouvert parade draws musicians and revelers to dance in the streets, and traditional folklore groups like the Clowns and Masquerades perform as they have for generations. It’s a rich celebration of history, the arts, food, and recreational pursuits that culminates on New Year’s Day.

New Year’s Eve in St. Barth

December 31 | St. Barth

Photo: La Plage

Photo: La Plage

Perhaps the most glamorous destination in the Caribbean, St. Barth is the place for celebrities, fashion icons, and spirited revelers to enjoy New Year’s Eve. Some of the most expensive yachts in the world gather near Gustavia Harbor in the week preceding the holiday, and many host exclusive New Year’s Eve parties on the water. St. Barth hotspots like La Plage and Le Ti St Barth are the clubs to be at on the island, and sometimes there are even pop-up clubs just for the dazzling affair. A spectacular fireworks display over Gustavia Harbor will bring in the new year.

New Year’s Eve in San Juan

December 31 | Puerto Rico

Another Caribbean destination for New Year’s Eve is the vivacious city of San Juan. Here the most magnificent parties take place in luxury hotels such as the Caribe Hilton Hotel and The Sheraton Hotel and Casino, as well as in chic beach bars with oceanfront rooftops. The hotels hold annual events such as The Sheraton’s Illusions that bring the region’s most talented DJs to the stage and special appearances by internationally known artists. Locals and visitors alike attend the spirited festivities that go well into New Year’s Day.