Time seems to stand still in Evora, a well-preserved medieval town that features protective walls, a 13th-century cathedral, several palaces,and a 1st-century Roman temple. No surprise that the town center is a UNESCO World Heritage Site. Even though it’s kind of creepy, don’t miss the Chapel of Bones, where the remains of nuns and monks are arranged in a haunting mosaic.

From Shoreditch’s swaggering style to Camden’s punky vibe and chic Portobello Road, London is many worlds in one. The city’s energy means that no two days are the same. Explore royal or historic sites, tick off landmarks from your bucket list, eat and drink in exclusive Michelin-starred restaurants, enjoy a pint in a traditional pub, or get lost down winding cobbled streets and see what you stumble across – when it comes to London, the possibilities are endless.

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.

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.

The next time you're driving to Toronto or Niagara Falls, stop in Hamilton, where tourist traffic isn't quite so rampant. The Niagara Escarpment provides spectacular scenery, with beautiful trails and waterfalls. Visit nearby farms, orchards and vineyards, or plan your trip to coincide with Hamilton's lively fall fairs.

Port of Spain, the capital of Trinidad and Tobago, has the tall buildings, neon lights and crowded streets of many cities, plus a multicultural Caribbean character and a home-grown calypso soundtrack. The best-known event is the flamboyant pre-Lenten Carnival. Among the city's other offerings are cricket and football matches, year-round festivals, a botanic garden, malls, an art and history museum and historic buildings. Entertainment options abound, but be cautious after dark.