Immortalized by Hemingway in “Islands in the Stream,” Cayo Guillermo is perched on Cuba’s north coast between the Bay of Dogs and the Atlantic. It is home to four all-inclusive resorts. Five miles of fine white sand and gorgeous, clear green waters, including the spectacular Playa Pilar, offer picture perfect sunning spots. Fantastic snorkeling and scuba diving opportunities beckon from more than six miles of coral reefs. Flamingos and many other birds live in its lagoons, forest and jungle.

U.S. citizens still need to jump through a few hoops to visit Cuba, but as visitors from around the world know, this island offers some amazing opportunities for cultural exchange. Havana is a mix of old-world architecture and of-the-moment culture. Head out of the capital city to the small town of Trinidad to see more Spanish colonial architecture. It’s a UNESCO World Heritage Site and a fantastic home base for a visit to the Valley of the Sugar Mills, a pocket of land that formerly served as the centre of Cuba’s sugar industry.

Travelers come to this small island north of mainland Cuba to bask in the sun, swim in sparkling blue water, and be pampered at an all-inclusive resort. To explore Cuban culture, you’ll need to go farther afield (this is a planned resort development; employees are bused in), but if you’re simply looking for a stress-free tropical break, Cayo Santa Maria might be perfect for you.

Cuba's top beach destination sits on a 13-mile-long peninsula with powder soft sands lapped by waters of the Kawama Channel. Resort hotels teem along the shore that U.S. celebrities and gangsters, including Capone, discovered in the 1920s. Clubs and bars provide mojitos and merriment, after long days baking on the beach, golfing, diving or deep sea fishing. Rent a scooter or hop aboard an open-air tourist train or bus to see more of this stunning spot. Caves, keys and virgin forest add to the area's allure.

There are no two identical Bahamas holidays. With options as diverse as its 700 islands, the Bahamas may seem schizophrenic: is it a family destination, a place for lovers to sneak away, a gambling mecca, a cruise-afficianado’s chief port of call or a shopper’s world market? The answer is, yes. It’s that, too.

Jamaica is a melting pot of African, Asian, European and Middle Eastern cultures. You'll experience this diversity in its strong crafts tradition, performing arts and distinctive dining options, like ackee and saltfish with roast breadfruit. Take your holiday to new heights at famed cliff jumping spot, Negril Cliffs. Jamaica offers long beaches, protected coves, rugged mountains, waterfalls, caves and sunshine and chances to play in the surf, ride horses and swim with dolphins. Jump in!

It’s not just for spring-breakers. Cancun, with its golden beaches and perfect climate, is the premiere coastal destination in Mexico. And while there is certainly a 365-day party available for college students, resorts cater well to families and to those seeking solitude. This Yucatan paradise is also the gateway to the ruins of Tulum and Chichén Itzá.

Stretching from the fishing village of Puerto Morelos to the biosphere reserve of Sian Ka'an, the Mayan Riviera offers an unforgettable Caribbean coastline experience. Divers and snorkelers will be dazzled by the wrecks of Xcaret and the Puerto Morelos reef. Use a zip line to descend into the sacred subterranean caverns of LabnaHa Eco Park, where you can snorkel an underground river under a canopy of stalactites. The nearby Tulum Monkey Sanctuary will put you in a playful mood.

The Dominican Republic lies in the same waters as Cuba and Puerto Rico, taking up the eastern two-thirds of the island it shares with Haiti. Offering a lush interior with a mix of caves, Victorian gingerbread houses and the lore of pirates, plus 900 miles of coastline along its brim, island highlights include riding a cable car up Mount Isabel de Torres and basking on stunning Saona Island. Oh, and did we mention the D.R. is family-friendly, has just about perfect weather and is affordable?

Among the best golf destinations in the world, Punta Cana is the very picture of leisure. Several of the courses have been designed by professional golfers, making for the perfect sort of kicked-back challenge that you want on a golfing vacation. The beaches here are simply perfect: calm, warm waters that gently lap at stretches of fine white sand. Thrill yourself with a zip-line adventure, clap along with traditional Dominican music at a cultural performance, or explore the magical lagoons of the Indigenous Eyes Ecological Park.

Visit Aruba once and you'll instantly start planning your next visit. The island wins you over with gorgeous weather, serene beaches, exciting land and sea activities (ATVs in the outback, anyone?), and terrific nightlife, from restaurants to casinos and nightclubs. Don't miss the live music scene, featuring Aruba's own Tumba music.

Dozens of nightclubs, hundreds of restaurants and some of Mexico's best beaches await you in Puerto Vallarta. The original colonial town still shines through an endless selection of shopping, art galleries, water and land activities, and hotels. Walk the malecon (boardwalk) and just try to take it all in.

You'll find crashing waves off Cabo's Pacific coast and sheltered, calm water on the Sea of Cortez. Given those options, Cabo has built a rare reputation for both excellent outdoor sports (big-game fishing, diving and kayaking, among others) and pure beach relaxation. Of course, there's also great nightlife. Cabo’s resorts, hotels and inns cater to everyone from honeymooners to families to Hollywood stars seeking a weekend getaway.