A night at Antigua’s Curtain Bluff for $80, including breakfast and dinner? How about a suite and all meals at Little Dix Bay on Virgin Gorda for $125? It’s hard to believe, but those were the going rates in the first edition of my guidebook "Caribbean Hideaways", published in 1978. Thumbing through it recently, I was delighted to discover that many of my favorites from back then have retained their places in the Caribbean pantheon and are still going strong. Three decades at the top is an extraordinary achievement, what with new resorts opening every other month, each hailing itself as the last word in style and service.
So how do the classics do it? Here’s one theory: New resorts have business plans while the classics have innkeepers. Many of the golden oldies are still owned and, in some cases, still managed by their founders, who are tirelessly devoted to their properties. In many ways, these venerable resorts are younger than ever. Along with the perpetual maintenance required to counter the challenges of a tropical climate, these hotels also have to keep pace with the tastes and expectations of the children and grandchildren of their longtime guests, and to attract a new clientele. So they have gradually (and sometimes reluctantly) modernized, installing flat-screen televisions, Wi-Fi and air conditioning and relaxing dress codes while staying true to their original spirit and sense of place.
Since it’s probably safe to say that no one has been rating resorts in the Caribbean longer than I have, I feel qualified to honor the region’s classics. Choosing only 10 wasn’t easy, so I applied this yardstick: The resort must have been around for at least 30 years, remaining at the head of the class for most of them. I also considered the condition of the property; the quality of its cuisine and the ambience of its restaurants; the range of activities available; value for money; and, of course, the standard of service delivered by its staff.
Anse Chastanet, St. Lucia
“We want our guests to feel connected to the surroundings,” says Nick Troubetzkoy, the visionary architect who owns this enchanted hillside resort with a view of a UNESCO World Heritage Site, the twin volcanic peaks known as the Pitons. Troubetzkoy scrapped the traditional, four-walled room model and designed Anse Chastanet’s rooms with one wall missing, allowing guests to fully enjoy the eye-popping panoramas of sea and sky. (“Nick’s Russian family tree includes plenty of revolutionaries,” notes his wife and general manager, Karolin.) Accommodations are more than 100 steps up from the beach (as is the hotel’s swanky sister resort, Jade Mountain), but at sea level guests have everything they need, including a dive shop and a fleet of mountain bikes for exploring the plantation grounds next door. From $280 in low season ($450 high); 49 rooms; 800-223-1108; ansechastanet.com
Bitter End Yacht Club, Virgin Gorda, BVI
With spas, casinos, boutiques and all the other fancy land-based features designed to lure guests to modern resorts, it’s easy to forget the Caribbean is a sea. Not so at Bitter End. Tucked away on Virgin Gorda Sound, this place is as much about sailing and scuba as it is about tanning and dining. Room rates include unlimited use of more than 100 sailboats and powerboats, and 15 excursions to surrounding islands (including a weekly catamaran trip to remote Anegada) make the hotel one of the Caribbean’s best values. The Hokin family wouldn’t have it any other way; they bought Bitter End as a private retreat in 1973 and ended up opening it as a resort where other clans can share in all the nautical fun. From $650 in low season ($890 high); 85 rooms; 800-872-2392; beyc.com
The Buccaneer, St. Croix, USVI
This pink-and-white confection of a hotel, splashed across a hillside near Christiansted, recently celebrated a landmark birthday, the big 6-0. The historic estate goes back to pre-Danish-colonial times (when it was owned by a Knight of Malta), but the Armstrongs, owners since 1947, maintain it so meticulously that every stucco wall appears to have been painted just yesterday. “A cornerstone of our success,” says third-generation owner Elizabeth Armstrong, “is our family’s absolute commitment.” That’s also demonstrated by the outstanding hospitality delivered by the long-serving and welcoming staff — one significant reason, no doubt, why a guest recently celebrated his 50th vacation at The Buccaneer. From $280 in low season ($340 high), including full breakfast; 138 rooms and suites; 800-255-3881; thebuccaneer.com
Coral Reef Club, Barbados
Take the best country-house hotel in England, plop it down on the Platinum Coast of Barbados, and you’ve got the Coral Reef Club — gracious, refined and understated. Acres of flowers and shade trees embrace an estate villa built of coral stone whose luxury suites, dotted around the garden in low-rise wings, offer some of the Caribbean’s most elegant lodgings. “Our guiding philosophy,” says Patrick O’Hara, the founder’s son, “is to offer our guests a high-quality experience by encouraging a truly friendly, family atmosphere through our own family involvement.” The O’Haras’ task this summer: a brand-new spa built, naturally, of coral stone and surrounded by hibiscus, cassia and allamanda blossoms. From $385 in low season ($760 high); 88 rooms and suites; 800-223-1108; coralreefbarbados.com
Curtain Bluff, Antigua
“I have lived at Curtain Bluff for almost 60 years,” notes owner Howard Hulford, “and our guests are like extended family whom we always look forward to welcoming home.” No idle boast: I was there for the resort’s 40th anniversary, and it was exactly that — a reunion, with some celebrating their 30th or 40th visits to Curtain Bluff. Over the years Hulford has slowly, sometimes grudgingly, acknowledged the 21st century, adding air conditioning (with units carefully tucked out of sight) and a spa. But guests still dance to live music beneath the old tamarind tree, there still aren’t any TVs in the rooms and there are still no locks on the doors. From $645 in low season ($995 high); 72 rooms and suites; 888-289-9898; curtainbluff.com
Jamaica Inn, Jamaica
“I was brought up at the inn,” notes Eric Morrow, owner of the intimate Ocho Rios hotel, “and my children are here now, the third generation of Morrows.” The family’s haven is a private cove with 700 feet of soft sand alongside lawns and flowering shrubs. Spacious suites feature lanais that function as outdoor living rooms furnished with plump upholstery. Every night there’s dinner and dancing under the stars on a broad terrace bordered by white balusters and tall coconut palms. And there’s nothing more romantic than a moonlight massage for two in the small Polynesian-style spa at the edge of the cove, surrounded by fragrant flowers and candles. From $290 in low season ($550 high); 49 rooms; 800-837-4608; jamaicainn.com
La Samanna, St. Martin
When it threw open its royal-blue doors in the early ’70s, this Mykonos/Moorish getaway was a hit with the luminaries of the time. I once sat two tables away from Richard Nixon and Billy Graham, wondering why on earth they would be staying at such a sexy resort (probably because of then-owner James Frankel’s reputation for ruthlessly protecting his guests’ privacy). Now owned by Orient-Express Hotels, La Samanna may have lost some of its mystique, but it still whispers romance the minute you drive in through its resplendent garden. Some beachside suites have private rooftop terraces for star-spangled canoodling, and the restaurant reserves the best tables (with views of a mile-long beach and an endless moonlit sea) for twosomes. From $395 in low season ($995 high); 81 rooms and suites; 800-854-2252; lasamanna.com
Round Hill Hotel & Villas, Jamaica
Not all classic resorts represent the vision of a single hotelier. This one’s owned by a committee, a group of billionaires and aristocrats who own its 27 shingle-roofed villas. Yet it still retains its distinctive cachet and refined daily rhythms. Next-door neighbor Ralph Lauren recently restyled the beachfront hotel suites, but for the authentic Round Hill experience, check into one of the villas, with private pools and staff who probably cooked breakfast and made beds for Oscar Hammerstein, Cole Porter and Jackie Kennedy. Guests and owners mingle merrily at weekly cocktail parties and beach barbecues where everyone dances in the surf. From $370 in low season ($620 high); 27 villas plus 110 rooms and suites; 800-972-2159; roundhillhotel.com
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