Entertainment can be experienced in a variety of ways in Santiago de Cuba.  Your ears may find comfort in the Casa de Las Tradiciones, a venue of the Trivoli neighbourhood where Cuba's finest musicians gather for improvisation;  your mouth, in Paladar Salon Tropical, where mainstays of the national cuisine arrive in generous portions; your eyes, in the Jardin de Los Helechos, home to a floral explosion of 90 types of orchids and 350 types of ferns.The gentile Tivolí district, some of Santiago de Cuba's most exciting ensembles, singers and soloists take turns improvising. Friday nights are reserved for straight-up, classic trova, à la Ñico Saquito and the like.

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.

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!

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.

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 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?

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.

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.