Cayman Islands
At either of two small beach resorts on Little Cayman, you can dive well and dine well—and which activity you prefer may determine your choice. A quirk in these glitz-and-glitter islands, Pirates Point Resort has real Caribbean spirit. Texan Gladys Howard, charming owner of the informal beach-bound resort, has chefed with James Beard, Jacques Pepin, and Julia Child, so you'll eat yourself silly. And you'll return. (Most guests are repeats, and a colorful lot they are.) The simple rooms—there are only 11, of which 5 have air-conditioning—are set in airy groves of palm, sea grape, and casuarina pine, and have wicker and rattan furniture and colorful throws. Near the southwestern tip of the island, it's a quick ride to Bloody Bay and some of the best diving in the world. The resort has dive packages and five instructors. If you're more of a floater, there's a swimming pool and one of the world's larger hot tubs, which holds ten hydrophilic guests at a time. Rates are all-inclusive (345-948-1010; piratespointresort.com; doubles, $180; v).

Reverse the emphasis at the Southern Cross Club—a good kitchen, but one of the best dive operators in the world. It is also the poshest place on Little Cayman—luxury in a pristinely natural setting. The spiffy pastel-painted resort has just 12 rooms on a vanilla-cream, standard-setting beach on South Hole Sound. Besides diving, there's deep-sea and freshwater fishing, and kayaking to deserted Owen Island. Rates are all-inclusive (345-948-1099; www.southerncrossclub.com doubles, $330).

Curaçao
Got a case of the blues? Revel in them at the Avila Beach Hotel's new Blues Wing, built along a reinforced dock. Each of the 20 big rooms has local paintings, a kitchenette, an oversized whirlpool, and a deck. A sax-playing silhouette decorates the door to your room, and the sliding glass doors facing the water reveal passing ships by day and the firefly lights of the capital, Willemstad, by night. The mile-long ribbon of sand is edged by the hotel's crayon-colored buildings, including the original 18th-century mansion and the small La Belle Alliance theater, where classical music is performed by mainly European artists. Thursdays and Saturdays there's live jazz at the Blues bar and restaurant, built on another sea-washed dock (5999-461-4377; http://www.avilahotel.com doubles, $115-$200; v).

Grenada
A somewhat faded main house anchors a complex on the southeast coast. Welcome to La Sagesse, and the old Caribbean that many travelers still seek. Of the 12 rooms, the 3 new ones are preferred. But it's the setting that matters, in the midst of Grenada's Nature Centre. Much of the half-mile beach is rather rocky, but one stretch of pounded-powder sands beckons amid the mangroves and lush palm trees. A finger of freshwater terminates on the property, creating year-round greenery, and there's a salt-pond bird sanctuary, twisting but marked hiking trails, and a restaurant with good fresh fish and local specialties (473-444-6458; www.lasagesse.com doubles, $80-$105; v).