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.

You've got to walk the Freedom Trail the first time you visit Boston. That's just a given. Make sure you step off the line on the pavement, though, and explore some of Boston's fine museums (try the Gardner—art masterpieces displayed in their collector's mansion) and old neighbourhoods (like the North End, where you can get the best cannoli this side of Italy). You can't claim to have experienced real Boston culture, though, unless you've watched a Red Sox game from the bleachers.

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.

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.

The first time you go to New York, go ahead and be a sight-seer—everyone should visit the Statue of Liberty, the Met, Times Square, etc. But on a return trip, pick a neighbourhood and go deep. You’ll find hole-in-the-wall bars, great delis, quirky shops�� exploring the non-touristy side of New York is an incredibly rewarding experience for a traveller.

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.

Toronto's neighbour Mississauga has more than 480 parks and woodlands for you to explore. Stroll the Waterfront Trail, rent a boat at the marina or spend a day at the racetrack. It's also called Ontario's shopping capital, with everything from shopping centres and outlet malls to picturesque village-style shopping streets.

If you’re a history buff and a die-hard foodie, Chicago’s your kind of town. Take an architectural-history walking tour, then dine at Alinea (the most celebrated molecular-gastronomy restaurant in the U.S.). And don’t miss the Museum of Science and Industry, the biggest science museum in the Western Hemisphere.