Off-Season Is the Right Season: 6 Caribbean Islands to Visit This Fall

The Caribbean is always a sought-after destination for northerners looking to escape winter’s chill, but if you want to avoid the crowds and high-season rates, autumn is the time to go.

While September through November is considered the rainy season for some islands, typically you won’t have to worry about anything more than an occasional passing shower or a few cloudy days (aka the perfect time to hit the spa!).

Plus, fall is a great time to experience island culture thanks to the season’s arts and music festivals, restaurant weeks and sporting events. Here’s what to do this autumn on six Caribbean islands.

Saint Lucia

Because of its mountainous setting, there is a stronger chance of rain in Saint Lucia in the fall, but showers pass quickly and are followed by clear blue skies and a vibrant green landscape.

Mid-September brings Saint Lucia’s premier food event: the Food & Rum Festival, where homegrown chefs like Nina Compton and Shorne Benjamin join wine connoisseurs, food critics, rum distillers and other chefs from around the world for cooking demonstrations, rum and wine tastings, chef dinners, and reggae and calypso music.

October is Creole Heritage Month, a celebration of Saint Lucia’s French Creole cultural, ethnic and artistic heritage through musical and theatrical performances, street fairs, seminars and lectures, art exhibits and, of course, delicious food.

Creole Heritage Month culminates during the last weekend of October with the celebrations of International Creole Day (Jounen Kweyol) in communities across the island.

Turks and Caicos

October in Turks and Caicos brings less-oppressive temperatures and calm waters, so sport fisherman will want to take to the ocean for in-season tuna, wahoo, mahi-mahi, sailfish and spiny lobster.

Foodies should plan their trip around major culinary events like the Caribbean Food & Wine Festival, held in late October, where chefs from around the world celebrate with five days of gourmet dinners, tastings and a food fair.

The end of November brings two major events: the Conch Festival, which honors the island’s national symbol through traditional and unique dishes like conch fritters, conch chowder and conch empanadas, and the Turks and Caicos Unity Festival, which features a fashion show, battle of the bands and concert.

Families on vacay will love Museum Day in early November at the Turks & Caicos National Museum, where there are free games, food, drinks, prizes, live music and performances by local schoolchildren.

Aruba

Enjoy Aruban cuisine throughout October during Eat Local Restaurant Month, where more than 65 restaurants offer prix-fixe lunches and dinners and take special care to incorporate authentic local dishes in their menus.

Don’t forget to pack a costume if your trip takes place at the end of October because Halloween is a big deal on this “one happy island.” Hotels and resorts are transformed into haunted houses, while spooky monsters, ghosts and zombies roam the beaches. Themed Halloween parties occur at several beaches, bars, lounges and clubs across the island, and little ones are invited to trick or treat at the hotels and resorts along the main drag in Oranjestad.

In November is the annual Island TakeOver Festival, a four-day urban and electronic music festival of beach parties, pool parties, international DJ’s and a major concert. Previous shows featured international artists J Balvin and Bad Bunny as headliners.

Bring home a unique keepsake from one of the 150+ exhibitors at the Aruba Art Fair, held in late November. The three-day event is filled with performances, hands-on workshops, children’s art classes and art tours.

Trinidad and Tobago

Carnival in Trinidad and Tobago (held just before Easter) is legendary, but there are also a ton of events to enjoy during the fall season on these sister islands.

Cycling fans won’t want to miss the Tobago International Cycling Classic held at the start of October, where professional and amateur riders battle it out on the challenging terrain while patrons enjoy the races against a backdrop of Caribbean festivities.

Mid-October is the popular Tobago Blue Food Festival focused on the root vegetable dasheen, also known as taro, that turns blue when cooked. The event is celebrated with a farmers market, tours of dasheen farms, crayfish catching competitions and live entertainment.

More than one-third of the population of Trinidad and Tobago traces their heritage back to India and honors their sacred traditions of Diwali, the Hindu celebration of light.

Celebrated in late October and early November in Trinidad’s East Indian communities, Diwali is a five-day festival featuring the lighting of lamps filled with coconut oil to welcome the goddess of light and lift spiritual darkness. The main event is Diwali Night, celebrated with light displays, singing and Indian food.

Grand Cayman

While on vacay, enjoy Cayman Restaurant Month in October for special prix-fixe menus and Cayman Cocktail Week during the last week of October for cocktail competitions, pop-up bars, cocktail tours, and Champagne and oyster parties.

Get your Jack Sparrow on during Pirates Fest, a week in November when thousands gather to watch a mock pirate invasion, a costume contest, parades, fireworks and much more.

If you’re the type that likes to work out on vacation, sign up for the Cayman Islands Marathon or half-marathon in early December, traversing through the capital city of George Town and alongside stunning Caribbean waters.

Barbados

Rihanna’s home island is absolutely flooded with fantastic festivals and events during autumn, and even though the fall months occur during what’s considered to be hurricane season, Barbados hasn’t seen one since 1955.

The festivities begin in mid-October during the Barbados Jazz Excursion & Golf Weekend, where jazz saxophonist and Barbadian recording artist Elan Trotman hosts a weekend of concerts, island excursions and charity golf for the annual tournament.

Late October is the island’s signature event, the annual Food and Rum Festival, drawing the best local, regional and international chef and mixology talent for a flavorful weekend of food, beach parties and, yes, rum-spiked cocktails.

Fitness enthusiasts can stay in shape during a 3.3-, 5-, or 10-kilometer race at the Open Water Festival in early November or at the Run Barbados Marathon Weekend, running through the beautiful capital city and UNESCO World Heritage Site, Bridgetown, in early December.