Distinctive architecture, sun-drenched resorts and eclectic small towns dot Andalusia, a dry, mountainous region of southern Spain that maintains echoes of its Moorish occupation. Spring and fall bring balmy temperatures, ideal for visiting Seville's cathedral, the world's largest Gothic structure, and the 1200-year-old mosque in Córdoba. Romantics love Granada, home to the Alhambra fortress and an inspiration to the late poet Federico García Lorca. Don't miss a dip in the sea along the Costa del Sol.

Originally founded as a Roman city and now home to three UNESCO World Heritage Sites, Seville is bursting with antique charm. The Alcazar palace complex is a stunning collage of architectural styles, and the Cathedral will impress you with its beauty and its status as the burial site of Christopher Columbus. The Metropol Parasol is the world’s largest wooden structure, a massive mix of grids and swirls that contains a market and a terrace observatory.

It’s nicknamed the Eternal City for a reason. In Rome, you can drink from a street fountain fed by an ancient aqueduct. Or see the same profile on a statue in the Capitoline Museum and the guy making your cappuccino. (Which, of course, you know never to order after 11 am.) Rome is also a city of contrasts—what other place on earth could be home to both the Vatican and La Dolce Vita?

Ottawa is a compact, clean, cleverly planned centre of culture and politics. And it's an ideal choice for a weekend getaway. Start downtown at the architecturally stunning National Gallery of Canada, and don't miss the Canadian Nature Museum and the National Aviation Museum. Rideau Canal offers boating in the summer and ice-skating in the winter. Gatineau Park attracts cyclists and walkers, while Byward Market blends old and new Ottawa.

We won't lie: Niagara Falls is uber-touristy. There are wax museums and a Ripley's Believe It or Not Museum, and if it's a fast-food chain, you can probably find it here. But even the most jaded hipster shouldn't pass up a chance to visit this town, because the Falls themselves are spectacular.

We've heard Toronto described as "New York City run by the Swiss," and it's true—you can find world-class theatre, shopping and restaurants here, but the sidewalks are clean and the people are friendly. The best place to start is literally at the top—the CN Tower, the tallest freestanding structure in the Western Hemisphere.

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?

Travelers come to this small island north of mainland Cuba to bask in the sun, swim in sparkling blue water, and be pampered at an all-inclusive resort. To explore Cuban culture, you’ll need to go farther afield (this is a planned resort development; employees are bused in), but if you’re simply looking for a stress-free tropical break, Cayo Santa Maria might be perfect for you.

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!

Key West has great nightlife—and a perfect cover story for someone who wants to enjoy it. A Hemingway fan simply must toss back a few at their hero’s favourite bar! You’re not reliving Spring Break, you’re immersing yourself in great American literature. Yeah. That’s the ticket.