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!

Even the sands of Playa Conchal are special, comprised of the silky remnants of millions of crushed conch shells. Frolic, swim and snorkel in the warm, crystalline waters by day; at night, camp out on the beach under the stars. Guided rafting, adventure and nocturnal turtle-watching tours are available—and exhilarating.

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?

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.)

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.