Culture-seekers will be charmed be La Isla's heritage and history, from Old San Juan's charms to folk art and festivals in the outlying towns. You can drive round Puerto Rico in a day, but take your time. Coffee plantations, colonial towns, beaches, bars and restaurants wait to be explored. Old San Juan, with famed Castillo de San Felipe del Morro, is an atmospheric place to wander. Experience life at a different pace by rainforest hiking, scuba diving or swimming Vieques' glowing bioluminescent lagoon.

Located on Puerto Rico’s north coast, Dorado is a resort town of relatively recent vintage. You’ll find luxury hotels and several championship golf courses. Of course, if you’re used to your local, scruffy public course, your score might suffer—gorgeous ocean views can be quite a distraction.

You don't have to choose between visiting a cultural capital or a sunny Caribbean beach destination—San Juan is both. This city's architecture ranges from Spanish colonial to 20th-century Art Deco, while the new Museo de Arte de Puerto Rico presents Latin American and Caribbean artwork in state-of-the-art galleries.

Once an important center for sugar production, Puerto Rico's fourth largest city's current fortunes come from its factories. Intriguing nicknames for the city of nearly 200,000 include The Land of Giants and Arm Hackers Town. Situated on the island's north shore, this Atlantic city is considered part of the metropolitan San Juan area. Popular attractions include Carolina Beach, Casa Escute art gallery, Caribbean Raceway Park and Isla Verde Mall. To make the most of your visit, consider renting a car.

Home to palm-lined beaches, tranquil coral reefs, and several top-tier hotels, it’s no wonder why Bavaro is one of the Dominican Republic’s most popular destinations. This resort hub combines convenience and Caribbean culture with an impressive range of activities across its expansive coastline.

Get the experience of visiting two island colonies in the same 37 square miles. Saint Maarten/Saint Martin's spicy marriage of Caribbean, French and Dutch cultures matches its physical diversity: the island is both urban and untamed, with rain forest-like landscapes, white beaches, and amazing caves and wildlife.

This Gallic toehold in the Caribbean exudes a distinctly French air, enticingly spiced up by West Indian warmth. Local culture and cuisine combine both influences. The stylish isle is dominated by Mount Pelée, which destroyed the city of St Pierre in 1902. Black sand beaches and rainforests are found in the north, with yet more beautiful sands to the south. Sights include La Pagerie, birthplace of Napoleon's Empress Joséphine, and Diamond Rock, a 600-foot pinnacle that was once registered as a British warship.

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.

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.

Refer to Vancouver Island as Victoria Island and risk a chorus of eye-rolls from the otherwise-friendly locals. Yes, Victoria is the main city on the island, but there are many distinct flavours to its logging and fishing settlements. Food and wine enthusiasts flock to the Comox Valley farm region, while the more outdoorsy types get their fix along the remote, forested beaches of North Vancouver Island. Visit the UNESCO Biosphere Reserve at Clayoquot Sound and you’ll return full of cocktail-party factoids.