Few things convey as immediate a sense of place to travelers as sampling local foods. Where to Nibble: Grand Cayman is host to the Cayman Cookout (Jan. 12–15), led by star chef Eric Ripert. At Jade Mountain Resort on the island of St. Lucia, visitors can embrace the freshness of the Caribbean with annual festivals that include Cooking in Paradise (March 22–26) with a Stairway to Heaven cocktail party, wine pairings and an exotic beach grill; and the Mango Madness Festival (June 13–18) when all things mango take over. Later in the year, Jade Mountain is the setting for the annual, highly anticipated Chocolate Festival, featuring Jade Mountain estate chocolate and cocoa-related events.

From April 7–10, celebrity chefs descend upon St. Croix in the US Virgin Islands for the St. Croix Food & Wine Experience, with events that include the much-lauded A Taste of St. Croix, along with the Cork & Fork Dinner, Sunset BBQ and Wine in the Warehouse. At the exclusive Grace Bay Club, the annual Caribbean Food & Wine Festival takes diners on a culinary tour of the island during a five-course meal with a fun twist: each course is served at a different award-winning restaurant (2017 dates TBA). Care to dine like a pirate? In Oistins, Barbados, November celebrates traditional flavors at the Barbados Food & Wine & Rum Festival (specific dates TBA).