Port Antonio Instead of Negril, Jamaica
Sidestep the well-trod resort destinations to the west in favor of this low-profile enclave just beyond the Blue Mountains on Jamaica’s northeast coast, sought after by the rich and glamorous since the fifties. This spring, the posh, thirteen-room Trident Hotel (from $450; tridentportantonio.com) was unveiled; it’s about a ten-minute drive from the luxury seven-room Geejam (pictured; from $395; geejamhotel.com), where artists like Drake and the late Amy Winehouse have come to quietly cut tracks at the on-site studio overseen by hotel owner–slash–music producer Jon Baker. As for the water, the Boston Bay has great surfing and jerk shacks, while the 186-foot-deep Blue Lagoon (yes, that Blue Lagoon), fed by a fresh mineral spring, is just as easy to get to (about a ten-minute drive from the Trident).
Gasparilla Island Instead of Palm Beach, Florida
It may have its fair share of immaculate golf courses, tony weekend mansions, and a lively social season, but the historic getaway of Gasparilla Island—wedged between Sarasota and Fort Myers—has a decidedly less stuffy vibe than Palm Beach, with just as much Lilly Pulitzer. Hit the charming time-warp town of Boca Grande, with its famous 1890s lighthouse, and check in at the storied Gasparilla Inn (rooms from $255; the-gasparilla-inn.com), featuring pastel Hollywood Regency–inspired rooms and the Pink Elephant restaurant (500 Palm Ave.; 941-964-4540), where you can nosh on retro favorites like shrimp cocktail and Key-lime pie. Catch your own snook in the bayou or go shelling on the island’s seven-mile stretch of beaches, and end the day with soft-shell crabs at local seafood joint Temptation (350 Park Ave.; 941-964-2610).
Culebra Instead of Vieques, Puerto Rico
Take the protected white-sand beaches and kayak-friendly waters of Vieques, subtract the fussy restaurants and slick boutique hotels, and you have Culebra, located just north of its bigger-sister island, off Puerto Rico’s eastern coast (Culebra covers only 11 square miles compared with Vieques’s 52). Expect decidedly non-glitzy accommodations, like the lovely twelve-condo Tamarindo Estates (from $149; tamarindoestates.com). Hop a kayak-and-snorkel excursion with Culebra Island Adventures (from $69; culebraislandadventures.com) and swim with sea turtles, or picnic on Flamenco Beach, a half-moon paradise flanked by swim-to reefs. For dinner, have a home-cooked meal at Barbara Rosa (195 Calle Escudero; 787-742-0773): Barbara fries up fish and chips in her kitchen while guests dine alfresco on her patio.