Stay: The Islander’s Inn (theislandersinn.net, 784-527-0944) is a newly opened, charming beachfront spot. Rooms start at $110 a night.
Do: In between festivals, get on a boat. The nearby Tobago Cays have some of the most stunning snorkeling in the Caribbean — turtles and all.
What do you get when Coney Island meets the Caribbean? Carnival Village in St. Thomas, the hub of the U.S. Virgin Island’s annual festivities. There’s a Ferris wheel. There’s beer. There are happy crowds of all ages. But there’s also Cruzan rum, “johnny cakes” — delicious fried rolls — and local “jam band” music, which has more beats per minute than just about anything on American radio. St. Thomas’ Carnival parade is small enough to feel homey, and it’s also injected with stateside flavor: bands perform choreographed routines as they parade, Rockette-style, down the streets of Charlotte Amalie in glittery costumes and knee-high boots.
Stay: The Ritz-Carlton (ritzcarlton.com/stthomas, 340-775-3333) is, well, a Ritz-Carlton — enough said. From $549.
Do: Join a mas band like the Caribbean Ritual Dancers — but only if you can get there early enough to practice that routine (or get good at faking it). Information: caribbeanritualdancers.com.
Don’t call it Carnival — it’s Crop Over. In Barbados, you don’t “play mas” on carnival day, as you do everywhere else, you “jump” with a band on Kadooment Day. Barbados has its own way of doing things, and you’ll find no quarrel with that because Crop Over, the region’s second-biggest Carnival, is the Caribbean’s hottest summer party. The name denotes its history — the festival has roots in the culmination of a successful sugar harvest, when slaves’ workloads decreased — but Crop Over is as modern a Carnival as they come, rivaling Trinidad in chic parties, barely there costumes and high-voltage musical performances. Since Barbados is a hub for soca music, Crop Over is a Caribbean music lover’s delight: a chance to hear new music rolled out in time for that grand march down the streets of Bridgetown.
Stay: The decor hardly screams “island,” but the Courtyard Bridgetown (marriott.com/hotels/travel/bgicy-courtyard-bridgetown-barbados/, 246-625-0000) is close to the action and filled with lively revelers, which means all Carnival, all the time. From $159.
Do: The Booze Cruise is not actually a cruise but a raucous Sunday beach party at a boatyard in Bridgetown, the island’s capital. What happens there, stays there.