Robinson Crusoe 2.0

Marisa Milanese
Single island
Caribbean resorts

Best Resorts

Gabe Weisert
Luxury Caribbean resorts

Ahoy, matey! Cuba’s second largest island – and the inspiration behind the pirate accounts in Peter Pan and Robert Louis Stevenson’s classic, Treasure Island – draws its historical roots from its swashbuckling counterparts. A prime destination for snorkeling, you may stumble upon a sunken ship or, if you’re really lucky, buried treasure. The jury’s still out on whether or not Uncle Sam taxes recovered gold left behind long ago by Long John Silver, Captain Hook and company.

If you've tired of the attitude of St. Barts, veer off course to Les Saintes instead next time around. With a similar, less pretentious clientele and a more kick-up-your-feet-and-chill environment, this up-and-coming cluster of tiny islands gives more bang for your buck. A place where you can still leave your door unlocked, Les Saintes has only two populated areas, Terre-de-Haut and Terre-de-Bas. Extremely French in every aspect, anti-Francophiles would probably do best to head elsewhere.

Although it's the largest island in the Bahamas, Andros - known by locals as "the Big Yard" - is also the least visited, even further adding to its appeal. With just 6,000 inhabitants, this haven for the shark-friendly is free of commercial tourism and boasts a host of virgin diving sites that have yet to be tapped along its 140-mile-long barrier reef, the world's third largest. Just don't get lost in the Tongue of the Ocean: the abysmal trench dips more than 6,000 feet below the ocean's surface and is a prime spot for wall diving.

Often confused with the Dominican Republic, which it is in no way affiliated, this tucked-away find appeals to naturists from far and wide. Influenced by its ever-changing, geothermal-volcanic activity, Dominica is home to the world's second largest boiling lake, as well as a plethora of flora and fauna. Dominated by rainforest and protected park, it also houses endangered wildlife that can no longer be found on its neighboring isles. "Dominica is lush and beautiful and a good choice for nature lovers - but it has black sand beaches, which may be a turnoff for some," says Sarah Greaves-Gabbadon, senior editor at Caribbean Travel & Life.

A lack of high-rises and all-inclusive package deals makes Tobago a diamond in the rough. With the Atlantic on one side, the Caribbean on the other and Venezuela's River Orinico running into its waters from the south, Tobago's surrounding sea is more emerald green than that encompassing other islands. Still, it remains popular with divers: Its coral community is impressive, and three ferry wrecks near the shore offer ample reasons for making the plunge.

Saint Kitts wins our superlative for "Most Likely to Become a Household Name," as the larger of the two islands that composes this sea-locked state has, unfortunately, turned into a stop on several cruise routes. Nevertheless, this tropical locale has maintained the hip, unassuming air that helped it gain popularity in the first place - if you venture outside its Disneyland-like cruise terminal, that is. A one-time sugar-manufacturing state, you'll still stumble upon dilapidated sugar cane fields and factories among the former British colony's hilly terrain. Just be sure and visit before the rest of the world discovers this well-kept secret. "Numerous luxury resort real estate developments are going up and additional cruise ships will be calling there year-round, so it won't be long before the crowds arrive," adds Greaves-Gabbadon.

One of nine islands that compose the Guadeloupe archipelago, Désirade is so remote it has a single modest road that runs under a steep limestone cliff. All of the island's villages are situated along this sole six-mile stretch. A fine example of the rural French West Indies of old, the desert-like Désirade features a bird sanctuary chock-full of wildlife, a host of hiking trails and a smattering of coconut trees along its coral-protected beaches.

With the majority of the island designated as protected park, don't look to Virgin Gorda for a Spring Break-like getaway. But if it's peace and quiet you seek, this BVI gem will deliver. Though it does see its share of tourists - its unusual natural attraction "the Baths," exotic grottos and pools formed by oversized boulders, insures a steady stream - most of the island tends to attract a more chill audience. Fun fact: Christopher Columbus lent Virgin Gorda its name (meaning "Fat Virgin") in 1493 for the landmark mountain that resembles a protruding tummy.

Unexplored and, thus, uncontaminated - it's called "the Unspoiled Queen" for a reason - this pinprick in the southern Caribbean is completely uninhabited in parts and is home to just over 1,000 residents. Gaining popularity for its diverse array of aquatic life and clear waters, giving it a diving visibility of more than 100 feet, Saba also sports miles of rocky coastline, making it prime territory for climbing and caving.

A major source of nutmeg, cinnamon, cocoa and cloves, Grenada - dubbed "the Spice Island" - has more spices per square mile than anywhere else in the world. It's also one of the Caribbean's most lush islands, with its mountainous interior and volcanic origins. "Grenada has it all: nice people, sandy beaches, good snorkeling and beautiful nature trails that wind through a colorful jungle," William Travis, editor of Frommer's Caribbean guide, says. "It's a very mellow, relaxing spot."

Around 1630, French buccaneers driven from Hispaniola settled this mountainous, rocky island off Haiti’s north coast, eventually attacking Spanish galleons laden with silver from South America and silks and spices from China. Henry Morgan, Francis L’Ollonais, and Pierre LeGrand settled here for at least some time. In the first Pirates of the Caribbean, this is the rollicking pirate town where Jack Sparrow and Will Turner recruit ranks into their crew.

In the Pirates of the Caribbean, Port Royal is where Captain Jack Sparrow is jailed before being freed by Will Turner. In reality, 16th-century buccaneers (pirates originally from Hispaniola) were encouraged by the British government to settle in this major shipping center and attack passing French and Spanish vessels. It endured as a hedonistic pirate enclave—the “Wickedest City on Earth”—until June 1692, when a massive earthquake sent a huge chunk of the town to the ocean floor, killing thousands. “Some considered the quake divine retribution for its sins,” says Marc Nucup of The Mariners’ Museum in Virginia.

It was only a small ramshackle village of tents and lean-tos made out of old sail cloth. But any Golden Age pirate worth his salt operated here for at least some part of the Golden Age—, like Calico Jack” Rackham, Anne Bonny and Blackbeard. This was the only fortified pirate republic in all of the Caribbean until the British sent Woodes Rogers, a former privateer himself, to drive the pirates from the Bahamas. By 1725, most were gone, and the islands’ motto became “Expulsis Piratis—Resituta Commercia” (Pirates Expelled—Commerce Restored).

During the Golden Age of Piracy, St. Croix was an unclaimed, largely abandoned island with a protected harbor and a good position on the Triangular Trade—perfect for a passing pirate hideout. In January 1717, a British man-of-war shelled pirate John Martel and his crew here; the survivors were left stranded and starving until two other pirate sloops arrived and absconded with them to Virgin Gorda.

With its jagged coastline of private coves and safe anchorages, this British Virgin Island was the hideout for all manner of bold-faced names, including Blackbeard and William “Captain” Kidd. For a couple of weeks in 1717, “Black Sam” Bellamy and his gang set up a temporary pirate camp in Spanish Town right under the nose of a British deputy governor.

Not much shipping passed within sight of La Blanquilla, just off the coast of Venezuela, making it a “good hideout for those trying to dodge authorities out of Barbados and French Martinique,” says author Colin Woodard, the author of a new book abour piracy's golden age, The Republic of Pirates. Just a few months after “Black Sam” Bellamy set up camp here in the 18th century, his flagship, the Whydah, sank off the coast off Cape Cod, where it was finally discovered in 1984; for the first time, some of those treasures will embark on a national tour in June, 2007.

Surrounded by narrow reefs and shallow channels inaccessible to merchant ships, Roatan became the base of hundreds of pirates in the 17th century, including buccaneer legends Laurens de Graff and Henry Morgan. From here, they staged attacks on Spanish galleons carrying Asian porcelain and Peruvian silver. Rumor has it that treasure hunters unearthed part of Henry Morgan’s cache here in the 1960s—and that there’s more to be found.

At the end of the 17th century, the French attacked this island with the help of a privateer by the name of William “Captain” Kidd. British by birth but French by employment, Kidd quickly turn-coated, stealing off with one of the French ships, according to Angus Konstam author of “The History of Pirates.” Kidd became an instant hero when he sailed to the British port of Nevis. Later accused of illegal pirating, he was executed and hung over the Thames River as a warning to would-be pirates.

According to Colin Woodard, Edward “Blackbeard” Thatch, who terrified victims by lighting candles in his beard and arming himself to the teeth, shelled this island on November 28, 1717. Leaving Guadeloupe town in flames (half the town was lost in the fire), he stole off with a French sugar ship.

The Cayman Islands’ position smack dab in the middle of the shipping channel between Mexico and Cuba made it a perfect stopover for pirates. Around 1722, one of pirate Thomas Anstis’s ships ran aground on Grand Cayman and he lost dozens of his crew to attacking British men-of-war who had sighted them. The islands still capitalize on their pirate history with an annual Pirates Week Festival in November.

At 1,800 acres, Peter Island, just five miles from Tortola in the British Virgin Islands, is the big daddy of our list. And, in this case, size does matter: Despite hosting more than 100 guests at a time along with boatloads of day trippers, "it's just big enough that you can carve out your own area," says Thomas Kohnstamm of Lonely Planet. One reason this was our critics' top pick: the brand-new 10,000-square-foot spa with its own pool. Other amenities include tennis courts, mountain bikes, and a fleet of sailboats.

For more information: Peter Island

With just 22 stone cottages scattered across 113 acres -- and the bespoke flag communication system -- Petit St. Vincent promises a complete removal from the outside world (nary a TV or phone in sight). "You're basically paying to be left alone here," said Doug Stallings of Fodor's. Our panel, who rated this second along with Jumby Bay, repeatedly cited the lack of pretension and attitude at the resort, which was designed and built nearly 40 years ago by a husband and wife who still live on site.

For more information: Petit St. Vincent

Since 2002, luxury chain Rosewood has managed the 50 suites and villas -- including 11 with their own plunge pools -- of this 300-acre island, which tied with Petit St. Vincent for second place. Because it's just seven minutes by boat from mainland Antigua, the resort feels less remote than other picks on our list. According to Terry McCabe of Altour, Jumby Bay is ideal for those "who want to be away but still want the ability to turn on CNN." With no minimum-age requirement (unusual for private islands) and a well-run nanny program, it's also ideal for families.

For more information: Jumby Bay Resort

If you and your 14 closest friends are good for $30,000 a night, this 45-acre island in the British Virgin Islands is all yours. "This is the island that everyone aspires to," says Doug Stallings of Fodor's, citing one reason that Necker, owned by Richard Branson, ranked third on our list. Two weeks a year, the island rents out its lavish Balinese lodging to individual couples (for a tidy $22,000 per couple per week); otherwise, the island is only available to groups.

For more information: Necker Island

Although just 135 acres, this island in the Grenadines has five private beaches and 37 guest rooms that were remodeled in 2000. The Tobago Cays National Marine Park, which offers some of the best diving in the Caribbean, is a quick boat ride away. Part of the allure of this speck of an island, which earned the fourth spot on our list, is undoubtedly its best-kept-secret status: According to Thomas Kohnstamm of Lonely Planet, "Even people who have heard of the Grenadine Islands still haven't heard of Palm Island."

For more information: Palm Island

"This place gets movie stars," says Doug Stallings of Fodor's. Indeed, Paul McCartney, Jerry Seinfeld and Raquel Welch have all vacationed at this 60-room resort styled in white with chic teak accents. Bruce Willis even owns a compound here. A Como Resort property, with tastemaker Christina Ong at the design helm, the property recently doubled its spa in size and has been winning awards for its yoga classes.

For more information: Parrot Cay

Johnny Depp and his crew bedded down here while filming Pirates of the Caribbean, squarely placing this 35-acre island on the map. But its fine sand beach, which earned high marks from our panel, was already considered the prettiest in the Grenadines. Thirty cottages are tucked into lush hillsides of hibiscus, ferns and flamboyant tree. And the island strikes an ideal balance between isolation and accessibility, according to Kay Showker, author of 100 Best Resorts of the Caribbean: "It's only 1,000 feet off the coast, but it's really all by itself."

For more information: Young Island

Guana Island likes to cite its stats: 850 acres, 36 guests, seven beaches. Yet the beauty of this island off the coast of Tortola is less quantifiable: It's a designated wildlife sanctuary with mountain trails and a range of endangered species. The ideal guest here, says Janet Groene, author of Personal Paradise: Caribbean, is an adventurous soul: "It's for those whose idea of luxury is a place where you can wake up with the birds and fall asleep to a frog serenade."

Similar to Parrot Cay in size (800 acres) and location (a 25-minute boat), Meridian Club strikes an entirely different tone -- "less intense and celebrity-driven," says Doug Stallings of Fodor's. "You won't find as many movers and shakers here." What you will find at this resort, which earned seventh place on our list, are just 12 guest rooms and two miles of white sand.

For more information: The Meridian Club on Pine Cay

Even before David Copperfield bought this island in July, this resort was considered "the top of the food chain," according to Terry McCabe of Altour. Renting out only to single parties of 20 guests for $325,000 a week (that works out to about $100 an hour -- per person), the property has five guesthouses the size of small mansions. The 35-person staff fulfills every whim, from arranging special music performances to putting on beachfront fireworks displays.

For more information: Musha Cay