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."