True to its name, summer's annual Tobago Heritage Festival celebrates the cultural traditions of the island of Tobago and is considered the island's most important annual event. Festival events include food fairs, art exhibitions, live music, water sports, street parades and art markets over the course of the two-week event.
Photo courtesy of Trinidad and Tobago

The Captain Morgan Ironman 70.3 St. Croix, or "Beauty and the Beast" as it's affectionately nicknamed, features elite athletes from around the world who come to race in one of the Ironman's most scenic settings and face one of its steepest, most notorious hills in the sport, The Beast, along the bike portion of the course.
Photo courtesy of Marion Doss

Each spring, renowned chefs from around the globe gather in Cancun for the Cancun-Riviera Maya Wine & Food Festival. Besides the chance to meet celebrity chefs, festival attendees can partake in gourmet food tastings, interactive cooking challenges, wine and spirit tastings, dinners and lectures by some of the visiting chefs.
Photo courtesy of Boarding1Now/iStock

During the final week of April, the island of St. Thomas in the U.S. Virgin Islands throws its biggest party of the year, Carnival. The first festival was staged on the island in 1912, and today, it's bigger than ever, with boat races, food fairs, parades, costume contests, calypso music and a pageant to crown Carnival Queen.
Photo courtesy of Sherry Talbot Photography/iStock Editorial

In most parts of the world, St. Patrick's Day is a single-day event; in Montserrat, it's a week-long extravaganza that culminates in a grand celebration on St. Patrick's Day, the very same day when a slave uprising took place in 1768. Much of the action takes place in a simulated slave village, where attendees can feast on traditional foods, fly kites, listen to story tellers and see musical and dance performances.
Photo courtesy of David Mac Gillivary -Montserrat Tourist Board

You haven't experienced Christmas until you've celebrated the season in Puerto Rico, where festivities begin in November and continue on through mid-January. In the weeks leading up to Christmas Day, churches throughout the island hold mass with aguinaldos (Christmas carols), and the most important day is Nochebuena, a Christmas Eve celebration with a feast and midnight mass. Things wrap up on Three Kings Day with a large celebration in San Juan.
Photo courtesy of Raúl José

Memorial Day Weekend brings the Soul Beach Music Festival to the beaches of Aruba. This world-class R&B and comedy festival has featured top acts, like Kenny Edmonds, Robin Thicke, Ashanti, SWV and Ricky Smiley as headliners, with live DJ dance parties before and after acts take the stage.
Photo courtesy of Kia Clay

The biggest festival on the Barbados calendar, Crop Over, dates back to the late 18th century when it started as a celebration of the sugar cane harvest. For five weeks, the island is infused with a party spirit, with events like costumed parades, calypso performances, competitions, pageants, fireworks and rum ... lots and lots of rum.
Photo courtesy of Barbados Tourism Authority - UK

Carnival on the island of Trinidad is a raucous explosion of color, music and creativity just before the start of Lent each year. It's a party so wild and over the top that it purportedly makes Mardi Gras look tame. Pulsating soca and calypso tunes set the beat for dancing in the streets, pageants, steel drum competitions and parades galore.
Photo courtesy of Blacqbook/iStock Editorial

No one really knows just where Junkanoo originated, but anyone who's had the pleasure of attending is glad it's around. This iconic Bahamas street parade takes place on Boxing Day, New Years Day and sometimes also in the summer, and involves intricate costumes, loud music and troops of dancers shaking their hips through the streets.
Photo courtesy of Errol Bodie