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.

Set in rugged, mountainous territory in the east, Cuba's fourth largest city is known as the City of Parks. Columbus called the area the most beautiful land eyes have ever seen and much of the surrounding area hasn't changed. Officially called San Isidro de Holguin, the city's elegant plazas, scatter of colonial buildings and few museums make for a pleasant daytrip. More wonders lie offshore. Swim with dolphins in Bahia de Naranjo Nature Park. Dive to sites off Playa Esmeralda and Guardalavaca.

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.

The farther you go from Grand Cayman's busy docks, the more peace and quiet you'll find. At Stingray City (actually a sandbar), stingrays swim alongside you in the tranquil waters. Closer to town, travellers report finding some of the best massage and spa services anywhere in the Caribbean.

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.

One of the top diving destinations in the world for its bright storybook coral reefs, the island of Cozumel is also home to a variety of natural beaches. Choose a beach with soft white sand for relaxing, or snorkel off a rockier vista. A destination for both adventure and romance, Cozumel has a year-round Caribbean climate, untrammeled jungle and abundant nightlife.

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.

Is there a better way to cap off a day of pristine reef diving and heart-pumping adventure sports than by sipping a sunset cocktail? Didn’t think so! From ziplining to deep sea fishing to exploring the military-protected archipelago of Cayos Cochinos, the Honduran island of Roatan is a playground for lovers of water sports and ecotourism. Landlubbers will flip for the Carambola Botanical Gardens, a tour of the Stone Castle Cameo Factory or exploring the beaches on horseback.

Thirty-eight small, gorgeous beaches frame the turquoise waters around Curacao, and each one offers a distinct experience, from secluded to surrounded by cliffs. Scuba divers and snorkelers will find this a world-class destination, as will windsurfers and boaters of all kinds.

Are there more flamingos than people on Bonaire? It's possible, and it's part of this unspoiled island's appeal. Bring your binoculars and your scuba gear to make the most of Bonaire's natural charms: more than 200 different species of birds live here, and the island itself draws divers from around the world to its reef-lined coast, a National Maritime Park.