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.

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!

Cayo Coco, an island just north of mainland Cuba, has some of the world’s most gorgeous beaches—think superfine white sand and shallow, clear water. It’s popular with European travelers seeking a sunny escape at one of the island’s beach-side resorts. Snorkeling and diving are fantastic.

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.

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.

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.

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?

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.

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.