The city of Freiburg im Breisgau sits austerely on the edge of the Black Forest. Home to one of Germany’s oldest universities and a Gothic sandstone cathedral, it’s a hub for academics and medieval history buffs. Chug German suds at a local brewery, then hop a cable car up Schauinsland mountain, where astounding views and a solar observatory await.

Located on the Rhine River near the borders of France and Germany, Basel contains the country's highest concentration of museums. The culture-centric city, site of the world's most influential art market each June, is also home to the lovely Munster Cathedral, made of red sandstone with a multi-colored tile roof. Green spaces abound, including the popular zoological gardens in the city center. Switzerland's largest site of Roman ruins, Augusta Raurica, are an easy day trip to the east.

You view great wine as the essence of a good holiday. Your travel companion, however, is a beer aficionado. Will it be Paris or Munich? Stop arguing and go to Strasbourg, where you can have the best of French and German cuisine, including the booze. The entire central island is a World Heritage Site. Don’t miss the 12th-century cathedral or the storybook "la Petite France" neighbourhood.

The largest city in Switzerland is a major contemporary art and shopping destination. Important artworks are displayed in the Kunsthaus and the Rietberg Museum. Those who consider shopping an art can hone their skills along Bahnhofstrasse and Niederdorf. Chagall's stained-glass windows in the Fraumünster amaze. Zurich's 500 clubs and bars, including several in swimming pools, pulse with life till the early hours. This city on Lake Zurich has excellent public transport and a free bike-hire system.

Quebec City may be the only fortified city north of Mexico, but it welcomes visitors with open arms. Explore the Citadel, where you might catch Canadian troops staging a military ceremony. As for food, you could splurge on afternoon tea at the Chateau Frontenac, or do as the locals do and snack on poutine—french fries with gravy and cheese curds.

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.

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.

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.