Image: Jamaica Inn, Jamaica
Jamaica Inn
Along a private cove with 700 feet of soft sand, lawns and flowering shrubs, the Jamaica Inn, in Jamaica offers spacious suites featuring lanais that function as outdoor living rooms.
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updated 10/17/2008 9:30:48 AM ET 2008-10-17T13:30:48

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

Image: The Buccaneer, St. Croix, USVI
The Buccaneer
The Buccaneer, in St. Croix, USVI goes back to pre-Danish-colonial times.

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

Image: Caneel Bay, St. John, USVI
Caneel Bay
What distinguishes Caneel Bay in  St. John, USVI, is an exhilarating sense of openness.

Caneel Bay, St. John, USVI
What distinguishes Caneel Bay is an exhilarating sense of openness: 700 acres, seven beaches and a profusion of trees and flowers surrounded by two national parks, one on land and one underwater. Laurance Rockefeller’s vision was to create a retreat that would offer accommodations just a few notches above camping, with low-profile buildings of natural stone no more than two stories high and screened windows that let in the sigh of surf and the cooing of native doves. The windows have since been glazed, and the rooms are now air-conditioned, but there are still no phones or TVs, offering welcome solace to noise-jangled souls. As a guest once confided to me, “We’ve been coming here for over 20 years, and I think of my two weeks at Caneel as therapy.” From $395 in low season ($550 high); 166 rooms and suites; 888-767-3966; caneelbay.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

Image: Little Dix Bay, Virgin Gorda, BVI
Little Dix Bay
Little Dix Bay, in Virgin Gorda, BVI, welcomes guests to a virtual botanical garden boasting 50 varieties of palms, a grotto-like pool, and a secluded, Bali-style spa.

Little Dix Bay, Virgin Gorda, BVI
Little Dix is another of the trio of low-key resorts created by the late Laurance Rockefeller back in the ’60s and ’70s, oases that set the standard for service, serenity and settings — in this case a ravishing double curve of beach beside a reef-protected lagoon. Now a Rosewood Hotel, the resort still welcomes its guests to a virtual botanical garden boasting 50 varieties of palms. But a glance around reveals that once-virgin hillsides now sprout villas; there’s a new grotto-like pool beside the distinctive conical dining pavilion; and a secluded, Bali-style spa sits up on the bluff. Once off-limits to children, Little Dix now has a kids’ clubhouse so subtly integrated into the operation that even old-timers take families in stride. From $395 in low season ($750 high); 100 rooms and suites; 888-767-3966; littledixbay.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

Caribbean Travel & Life is the magazine for anyone in search of the perfect tropical getaway. Each issue presents expert insider’s advice on where to find the Caribbean’s best beaches and attractions, its finest resorts and spas, liveliest beach bars and activities, and its friendliest people.

Photos: Caribbean way of life

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  1. Barbados

    This undated photo courtesy of the Barbados Tourism Authority shows Harrismith Beach, Barbados. Sun, surf and sand are the main draws on this tropical Caribbean island. (AP) Back to slideshow navigation
  2. Barbados

    This undated photo courtesy of Barbados Tourism Authority shows The Watering Hole rum shop in Barbados. The rum shops on the island are good places to sample local food and drink, watch a game of dominos, or just get to know the friendly and hospitable Bajans. (AP) Back to slideshow navigation
  3. St. Lucia

    Developed, beautiful and situated in the Eastern Caribbean, St. Lucia is accessible from Europe and Canada, and reachable -- albeit not as easily -- from the United States. St. Lucia is known as a romantic destination. The island gets plenty of visitors, including wedding parties. (Holger Leue  / Lonely Planet Images) Back to slideshow navigation
  4. St. Lucia

    Cocoa pods lie on the ground ready to be processed at Fondoux Plantation in Soufriere, St. Lucia. Cocoa is one St. Lucia's main produce alongside the more obvious banana crop. (Chris Jackson / Getty Images) Back to slideshow navigation
  5. St. George's

    The capital of Grenada, St. George's is considered one of the prettiest harbor towns in the Caribbean. Grenada's unique layout includes many finger-like coves, making the island a popular sailing destination. (Richard Cummins  / Lonely Planet Images) Back to slideshow navigation
  6. The Cayman Islands

    The Cayman Islands very popular attractions, Stingray City and the nearby shallows known as the Sandbar, provide the only natural oportunity to swim with Atlantic Southern Stingrays. (David Rogers / Getty Images) Back to slideshow navigation
  7. Stingray City

    The Cayman Islands very popular attractions, Stingray City and the nearby shallows known as the Sandbar, provide the only natural oportunity to swim with Atlantic Southern Stingrays. (David Rogers / Getty Images) Back to slideshow navigation
  8. St John's

    In high season, up to five cruise ships visit St John's, Antigua, each day. The boats unload mostly American and European passengers who fan out across the island visiting the casinos and beaches. Antigua is easily accessible, and can offer good values for tourists. (Chris Jackson / Getty Images) Back to slideshow navigation
  9. Antigua

    Antigua, located in the Northeastern Caribbean, is a popular tourist spot. While there are high-end, stylish hotels, the island also features a large number of mid-priced options. Visitors will find beach bars, restaurants, casinos and shopping. (Richard I'Anson  / Lonely Planet Images) Back to slideshow navigation
  10. Antigua

    People walk along an area known as Devils Bridge in Indian Town Point, Antigua. Antigua is a wintertime destination for many visitors from the north. (Joe Raedle / Getty Images) Back to slideshow navigation
  11. Dominica

    Not as well known as other Caribbean islands, Dominica is green, fertile and mountainous. Visitors will find some opportunites to scuba dive, but watersports are not its main draw. The island does, however, offer a slew of rainforest trails -- great for hiking and sightseeing. (Greg Johnston  / Lonely Planet Images) Back to slideshow navigation
  12. Dominican Republic

    An old church building is seen in La Romana, the third-largest city in the Dominican Republic. (Wayne Walton / Lonely Planet Images) Back to slideshow navigation
  13. Belize

    Belize gets more than 850,000 visitors each year. The hot spot allows watersports such as kayaking and snorkeling, as well as inland activities like hiking and birding. The Mayan ruins of Altan Ha, pictured, are easily accessible from Caye Caulker. (Andrew Marshall / Lonely Planet Images) Back to slideshow navigation
  14. La Tortuga

    A fisherman repairs his nets on Cayo Herradura, off the island of La Tortuga in Venezuela. The country offers visitors a variety of activities to choose from, but remains undervisited -- especially compared to its South American neighbors. (Lynne Sladky / AP) Back to slideshow navigation
  15. Cuba

    Cuba blends the fantastic attractions associated with other Caribbean destinations with an amazing history. Tourists can stroll white sand beaches, take in the incredible architecture and party into the early-morning hours. (Javier Galeano / AP) Back to slideshow navigation
  16. St. Barthelemy

    St. Barthelemy is a vacation spot of stars and millionaires. Trendy, chic and sexy, St. Baarths is safe for tourists, but expensive to visit. About 8,700 people reside on the island. (Mark Mainz / Getty Images) Back to slideshow navigation
  17. Puerto Rico

    A man climbs to a 40-foot waterfall at the south side of the Caribbean National Rain Forest, commonly called El Yunque, near Naguabo, Puerto Rico. Most visitors hike the well-marked paths in the northern half of the park's rain forest but the trails in the south allow hikers and nature lovers to explore the only tropical forest in the U.S. national forest system. (Herminio Rodriguez / AP) Back to slideshow navigation
  18. Puerto Rico

    The cupola of San Juan Cemetary as well as colorful homes sit next to the ocean in Old San Juan, the original capital city of San Juan, Puerto Rico. The old city is a historic district of seven square blocks made up of ancient buildings and colonial homes, massive stone walls and vast fortifications, sunny parks and cobblestoned streets. (Joe Raedle / Getty Images) Back to slideshow navigation
  19. Puerto Rico

    Men play dominos in Old San Juan, Puerto Rico. Old San Juan is a well-preserved colonial city that allows tourists a peek into the past. (Joe Raedle / Getty Images) Back to slideshow navigation
  20. Guadeloupe

    Guadeloupe isn't as developed as some other Caribbean islands, but it offers a variety of beaches -- some active with watersports, some secluded. The island also offers beach bars, restaurants, mid-range hotels and other tourist amenities. (Marcel Mochet / AFP - Getty Images) Back to slideshow navigation
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