Port: St. Thomas, U.S.V.I.

This lively bar on the sand at Bolongo Bay Beach Resort is famous for two things: live music 365 days of the year and VooDoo Juice, a wickedly potent mix of five different flavors of Cruzan rum (coconut, pineapple, citrus, banana, and dark), plus cranberry and pineapple juices.

Port: St. Maarten 

Take a cab to Cul de Sac on the French side of the island, then catch a water taxi to Pinel Island, where you’ll find a glorious beach and this thatched-roof bar beloved by locals. Remember to bring a towel: There's a snorkeling trail nearby, and the bar has tables in the water.

Port: Aruba

Flanked by divi-divi trees and Palm Beach’s white sands, MooMba has the kind of Instagram-worthy Caribbean views that make you want to stay a while. Take a seat under one of two palapas, order the grouper or fish chowder, and wash it all down with bottles of Balashi beer, a local Aruban pilsner.

Port: Grand Cayman

If you haven’t sipped a mudslide since your college days, you may want to order one (or several) at this bar at the island's Rum Point Club. After all, this is where the vodka-Kahlúa-Bailey’s concoction was born. In between rounds, dig into conch fritters and jerk pork at the Crayola-colored picnic tables.

Port: Barbados

At this seaside joint in Bridgetown, the drinks are just the preamble. It’s the Caribbean spiny lobster — whether served in the form of lobster bisque or simply grilled — that’s the real reason to visit. Bonus: You’ll find live jazz here Tuesday, Thursday, and Saturday nights, as well as Sundays during lunch.

Port: Tortola, BVI

Bras and panties dangle from the ceiling of this ramshackle hot spot, famous for its wild full moon parties, potent rum punch, and eclectic décor. License plates, computer monitors, and graffiti are just a few of the colorful details.

Port: Punta Cana, Dominican Republic

Tucked away in the posh Cap Cana area, this cool joint sits on one of the prettiest beaches in the DR. Order a santo libre (rum and club soda) and dig into ceviche or a pizza in the shade before walking off your lunch on the white sand.

Port: St. Barts

This relaxed, relatively affordable outpost on Grand Cul-de-Sac is a delightful anomaly on ultra-chic St. Barts. Order anything seafood related (the conch fritters are especially good), then hit the shop to buy a bottle or two of La Gloriette’s infused rum to bring home.

Port: Martinique

This shack-on-the-sand in Le Carbet seems like your typical Caribbean beach bar, but look closer and you’ll find an extensive selection of rums and sophisticated Creole fare from chef Guy Ferdinand. Try the crayfish and scallops in vanilla sauce, which will give you serious bragging rights back on board. (It's worth the 30-mile trek north from Fort-de-France.)

Port: St. Maarten

For the photo op to end all photo ops, head to this watering hole on Maho Beach at the edge of St. Maarten International Airport. Planes fly so low as they land that you'll feel like you can almost reach up and touch them. Need something to entertain you between flights? Check out the crab races on the beach.