Few Americans have had the urge to go far afield this fall or winter, but the Caribbean is so close to home—and a hop to the tropics might be just what we need this holiday season. What I'm looking for is the feeling of being on solid ground and well looked after. I've gone back to the classics and picked out places that have been around long enough to run like clockwork while a guest winds down. Keeping cost in mind, I've included at least one fine budget hotel in each of the five categories that follow. (Rates and contact information appear at the end of the article.) These classics have all the requirements—talcum beach, glass sea, breezy terraces—and super service. With one exception, a new resort so satisfying that it qualifies for instant-classic status, they're all tried-and-true (but far from tired), and all of them, I'm glad to report, are worth another visit.
On the undeveloped southwest coast of St. Lucia, Anse Chastanet has a breathtaking view of the Caribbean's prettiest pair of mountains, the extinct volcanoes just offshore called the Pitons. The items in the rooms are proudly St. Lucia-made: the furniture, the art, the madras cotton bedspreads. The best rooms have walls of slatted wood that fold away to reveal sky, treetops and your own private Piton panorama, plus huge open-air showers. Some rooms you climb a hundred steps to reach; others are deep in tropical foliage; still others are on the ideal beach. The dive shop is famous, the chefs are superb (tropical world cuisine, they call it). This is one of the Caribbean's most unusual, most nature-loving resorts. Higher up around the bay, Ladera has the same Piton view—as well as big, big three-walled rooms (all are open-fronted, like tree houses), four-poster beds and private plunge pools, plus a well-thought-of casual restaurant, Dasheene. What's the catch here? No beach. Considering that the sea surrounds it on three sides, Biras Creek, on Virgin Gorda, has a surprisingly small beach, but you can always take a Boston Whaler (with a picnic lunch) to a deserted bay. High on the bluff is a cone-roofed, open-sided bar-restaurant, where the chef is the talented Swiss Jérôme Gottraux. Below, the simple, comfortable, if not hugely beautiful rooms, look out on the waves. (Skip the claustrophobic garden rooms.) There's tennis, water sports, a pool, a library, a TV room, acres of trails, and bikes to explore them, and blessed peace. The locally owned Fat Virgin Café on one of the docks is a must. Budget: Asa Wright Nature Centre and Lodge. Deep in Trinidad's rain forest, these wooden one-room bungalows set around a nicely shabby Great House belong to one of the earliest eco-tourism resorts—nothing short of a bird-watchers' heaven.
For 30 years, the Hokin family has run Virgin Gorda's remote, raucous, sprawling, every-sport-under-the-sun-or-in-the-water Bitter End Yacht Club. You can sleep on a boat or in a villa—the thatched Swiss Family Robinson ones that they call Beachfront are the best—and join the legions of Americans who consider this resort their second home. Kids love the barbecue-and-seafood menu. Expect tears when it's time to leave. To call Anguilla's famously elegant 17-year-old Malliouhana child-friendly may seem counterintuitive. But this grand cliff-top resort in late-'60s Palm BeachmeetsFrench Riviera style, all white tiles and glass tables and bamboo sectionals, offers what you might call remote-control parenting. For the kids: a new, supervised, supersize playground. For you: the renowned French chef Michel Rostang, a notable 25,000-bottle cellar, floodlit tennis courts and a spa that's scheduled to open late next year. For the whole family: outsize rooms with grand terraces, two beaches and five freshwater pools. Budget: Blue Horizons Cottage Hotel. In high season, under-12s sleep free (in low season, under-18s), making the Mediterranean-style apartments at this six-acre Grenada resort irresistible—especially since world-class Grand Anse beach (with the hotel's grander sister, Spice Island) is steps away. The restaurant, serving Frenchified local food, is a Grenadan hot spot.
There is no escape farther from day-to-day reality than a private island—though let's not pretend the check won't bring you back to earth. For the lucky few, Necker Island offers the ultimate seclusion—because here every one of the guests (26 maximum) is invited by you. The bare, beachy, 74-acre British Virgin island was transformed 27 years ago by Richard Branson (CEO of, appropriately, the Virgin Group of Companies) into an Indonesian-looking playland, with elephant-bamboo furniture by Balinese artisans—a style that's caught on all over the West Indies. You get a 31-member staff, various boats and libraries (CD, video, book), two tennis courts, four pools, plus all meals and even alcohol. To avert a Lord of the Flies scenario, you should settle beforehand which of your tribe gets the alpha bedroom—the whole top floor of the Great House. Another of the British Virgins, Peter Island, is rightfully proud of its just-redone suites on the perfect white crescent of Deadman's Bay Beach. The less spectacular, regular rooms have also been redone; they surround the cute marina (with dive shop), seaside pool and open A-frame bar-restaurant. The place is wonderfully huge: nearly 1,200 acres, with five fine beaches, an incredibly friendly longtime staff, free boat trips, a petite new spa and gym, and two good restaurants, one Asian-Caribbean, the other beach-casual. Budget: Richmond Great House. Owned by Hollis Lynch, professor of African history, this eccentric late-eighteenth-century country inn is set high on a hill in Tobago. The experience comes complete with gorgeous green grounds, swimming pool, collection of African art, 10 plain-Jane bedrooms and lovely home-cooked dinners.
With its empty beaches, fantastic villas and matchless serenity, Mustique, the verdant island in the Grenadines that was once Princess Margaret's playground and is still Mick Jagger's, just about defines romantic. And it now has the hotel to match, since the Cotton House has spent the past couple of years becoming the perfect retreat. Its exuberantly landscaped grounds contain seven cottages with a mere 20 quiet and private rooms, all with pickled-pine furniture, four-poster beds and CD players; most have big balconies as well. A spa and a beach restaurant are scheduled to open in the spring. In the plantation-style Great Room there are squashy sofas, a bar and veranda tables for fabulous French chef Jean-Jacques Ugé's dinners (breadfruit gnocchi, grilled catch of the day). It's even an excellent value, since the rates include everything but bar drinks. Anguilla's Cap Juluca also keeps on getting better; it should thank Hurricane Lenny, which necessitated the rebuild that was completed late last year. Eighteen slightly kitsch white Moorish structures line the mile-long Maundays Bay. Some have white-tiled balconies and small gardens leading out to the sand; others, gigantic bathrooms with two-person tubs; still others, private rooftop terraces. The combination of the space, the sea view and the privacy makes them probably the sexiest rooms on the islands. The three restaurants run from a casual one on the beach to a sort of sultan's palace without walls that offers sophisticated but unfussy dishes (grilled tuna with caramelized fennel). Budget: Lagoon Marina and Hotel. This one's for yacht-lovers: an intimate 19-room garden-set hotel on the south coast of untouristy St. Vincent, overlooking its own marina and a narrow black-sand crescent beach. Try to get one of the sea-front rooms, with simple white walls, high ceiling and terrace—perfect for a couple.
A direct flight (from the East Coast) and a half hour by limo, and you've reached the only inland hotel on Barbados, the brand-new Villa Nova, a serenely rural plantation estate that was once British Prime Minister Sir Anthony Eden's home. Now, thanks to the witty patrician interiors of British design star Nina Campbell, it's fantasy English tropical country house, with a grand piano; a well-stocked library; carmine or buttermilk walls and covetable antiques in the bedrooms; and bathrooms with claw-foot tubs and dinner-plate showerheads. The chef, Garry Knowles, who was poached from London's trendy Ivy restaurant, brings astonishing range to the menu, which changes daily (sea bass with green Thai curry and soba noodles, tuna with tapenade), in an up-to-the-minute style quite new to the West Indies. The grounds are a fairyland; the big beach (a 10-minute drive away) is thrillingly wild. Antigua's Curtain Bluff is also just a one-flight-one-drive hop from the East Coast. Howard Hulford, the owner, has just celebrated the 40th anniversary of his meticulously groomed and organized hotel. That means four decades of refinements—like the food-import company he founded when one of his chefs was disappointed with the local supplies, and the spectacular wine list (over 25,000 bottles) heavy on Burgundies. The atmosphere is very country club, with jackets required for dinner and an understated decor of white tiles, rattan and pastels in the big rooms, and bedrooms that look out at either beach or scenic headlands. The rates aren't so steep when you consider that everything is included, even drinks, house wines and scuba dives. Budget: Paradores of Puerto Rico. More than a score of these basic but beautiful state-owned hacienda-style inns dot the Puerto Rican countryside. Some are close to San Juan, but an American Eagle flight from the capital to Mayagüez brings even the island's beautiful west coast within easy reach.