Named for Shakespeare's birthplace, Stratford has grown to become Canada’s premier arts town. In addition to the annual Stratford Festival, performing from April through October, Stratford is always filled with theatre, music and visual arts. The preserved 19th-century architecture and acres of parks and gardens (along its own Avon River, no less) are certain to charm. Stratford has also gained a reputation for culinary creativity, showcased at some of the finest restaurants in the country.

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.

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.

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.

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.

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.

Anne of Green Gables! There, we got that out of the way. Besides chasing the famous fictional heroine, you'll find Charlottetown's own history, culture and nightlife keep you more than busy. Enjoy outdoor activities from golfing to boardwalk strolls and biking by day, and theatre and performance arts by night.

Soaring mountains, jewel-coloured lakes and pristine wilderness await you in Canada’s first National Park. The irresistible beauty of the landscape invites travellers to immerse themselves in the outdoors all year round — whether hiking through untouched forests and paddling the turquoise lakes in summertime, or skiing the slopes and soaking in the steamy hot springs during the winter. Travellers also enjoy the warm hospitality of Banff or Lake Louise, the region’s charming mountain townships.

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.)

Amsterdam is truly a biker’s city, although pedaling along the labyrinthine streets can get a little chaotic. Stick to walking and you won’t be disappointed. The gentle canals make a perfect backdrop for exploring the Jordaan and Rembrandtplein square. Pop into the Red Light District if you must—if only so you can say you’ve been there. The Anne Frank House is one of the most moving experiences a traveller can have, and the Van Gogh Museum boasts a sensational collection of works.

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?