Jamaica
Relax. That's the point here—perhaps even more so than at most island resorts. Beach connoisseurs may fret at first sight of Jake's, but like we said, relax. Set on Treasure Beach, dead center on the south (Caribbean) coast, it is adjacent to a rocky beach that gets more and more sandy as you stroll along. And the cottages—there are only 15—are nestled into the landscape, some with decks just above the lapping sea. The cottages are painted in wild pinks, purples, and yellows, and each room has mosquito netting, candles, and a CD player. True to the spirit of the music biz entrepreneur who partially spawned the resort, there's a library of world music, and—how to put this?—a sort of foreign-legion outpost feel, with conscripts close to Jah and with ganja as well as rum at the bar. Lest you get too relaxed, there are mountain bikes and fishing and nature tours (876-965-3000; www.islandoutpost.com doubles, $105-$275; v).

The Jamaica Inn, in Ocho Rios, is one of those strange places that never seem to change yet keep on getting better. Well, there is a spiffy new spa and all the usual electronic gizmos, but the atmosphere remains slightly old-fashioned in the best sense, with staff who have been there forever and know your name. Oh yes, and it also happens to have one of the most beautiful small—and private—beaches on the island. Winston Churchill used to stay in the White Suite and set up his easel in the garden. Never noisy, never crowded, this is swimming and sunning at its most civilized. The Morrow family, from Connecticut, have owned the hotel since the 1950s, which must contribute to the feeling one gets of comforting continuity (876-974-2514; www.jamaicainn.com suites, $180-$325).

Mayreau
Talk about secluded: The smallest inhabited isle in the Grenadines is just a mile and a half square, with 3,000 feet of white sand beach, overhanging palms, sea grape trees, and no roads. The Saltwhistle Bay Club is the CEO's beachy bunker when the world (or his stock) gets shaky. Acres of trim gardens hide four simple two-story stone cottages, but nothing can hide the three-quarter-mile horseshoe beach or the barefoot-casual feel. Massive stone walls shape rooms, and curve to form circular stone showers. The suites are classically simple: cream and coffee fabrics, wooden shutters for that rare person who wants to shut out the magnificent vistas. The thatch-roofed restaurant on the beach serves fresh lobster and red snapper (784-458-8444; saltwhistlebay.com; suites, $360). A major night out would be a climb to Dennis's Hideaway, halfway up a steep hillside path created by goats, for goats. Chef Dennis Forde has a way with not only a skillet but also a guitar—and ask him about yacht trips on his 44-foot Irwin (784-458-8594; entrees, $17-$25).