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Catapulted to fame for its part in the 1988 Winter Olympics, this former coal-mining town in the Canadian Rockies is a perfect base for visiting some of the country’s most impressive national parks. First stop for most visitors is the ski trails in Canmore Nordic Centre Provincial Park. Contemplate natural wonders at the Museum and Geoscience Centre, and mush through the snow on a sled-dog tour.

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.

Known for its markets and its striking 19th-century limestone architecture, Kingston is a great base for exploring the Thousand Islands and the St. Lawrence River and its national park. Visit Wolfe Island on the free ferry, or hunt for antiques in nearby villages.

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.

Looking out over the city of St. John's, you may be reminded of a mini San Francisco (minus the cable cars). St. John's provides the ideal balance between nature and nightlife, from the East Coast Trail and its stunning scenery to the colourful entertainment district along George Street. Although it's the largest city in Newfoundland, the vibe is still very small-town. You'll feel welcome in the City of Legends!

Featuring white-sand beaches, volcanic peaks, and protected parks, along with some of the most impressive dive spots in the world, Guadeloupe is an island hopper’s paradise. This French archipelago is one of the Caribbean's best-kept secrets, offering a more relaxed alternative to its better-known neighbours.