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.

Rincon is best known for two things—surfing and sunsets. Beaches are small (meaning no huge resort beaches) and no matter how much of a Type-A personality you are, Rincon’s laid-back attitude and leisurely pace will soon win you over.

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.

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?

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.

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.

Montreal, c’est si bon! This French-speaking city is considered the cultural capital of Canada, and is a cosmopolitan celebration of Québécois style. A horse-drawn carriage ride around the cobblestone streets and grand buildings of Vieux-Montréal will give you a taste of European flavour. The Basilique Notre-Dame is a confection of stained glass, and the Plateau Mont-Royal district will delight you with its quaint boutiques and cafés. Dig in to a massive plate of poutine to fuel up for a tour of the epic Olympic Park.

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.

Is there any possible way Las Vegas could not be on our "best nightlife" list? The only way we could possibly omit it is on a technicality—since you can do pretty much anything 24/7 in Vegas, it might be wrong to call it "nightlife."

What happens when a "gassy" Englishman rows into town feeling thirsty? A pub is born. And from that a city—in this case Vancouver. Though the pubs are plentiful, food and drink aren’t the only things to take in during your trip. In its 150 years, Vancouver has grown into a cosmopolitan city nestled in the great outdoors. Enjoy the snow-capped mountains, waterfront forests, cityside beaches, Olympic history and the world’s highest suspension bridge. Hipsters welcome. (Don’t worry, they don’t bite.)