The oldest university in the world isn’t Oxford or the Sorbonne—it’s the University of Al-Karaouine, and you’ll find it in Fes el Bali. This walled city, a UNESCO World Heritage Site, will transport you back to mediaeval times. Visit the ancient maze-like quarters of the Medina to Fes el-Bali and the four imposing Gates of Fes, with their distinctive Moroccan tile work. You can walk, or, if you're brave, take a taxi—the daredevil drivers will have you hanging on for dear life.

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'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.

A cosmopolitan city known as the "cultural cradle of Canada," Winnipeg is family friendly with plenty of charm. It boasts a dazzling arts, theatre and indie music scene, as well as lip-smacking dining options to tantalize every taste bud. Experience nine acres of shopping and interactive fun at the Forks Market or explore Winnipeg’s diverse neighborhoods like the historic French Quarter and Exchange District or the boho chic Osborne Village.