Nestled at the tip of a promontory jutting into Lake Como, Bellagio boasts unparalleled shoreline and Alpine views. Add in boutique-lined cobblestone streets, Italian villas, and fragrant gardens, and it’s no secret why Bellagio is known as the Pearl of Lake Como.

A gorgeous spot that’s a convenient day trip from Milan, Lake Como recently earned fame as home to Hollywood star George Clooney. But celeb-spotting aside, it’s known for jaw-dropping natural beauty, elegant old villas—and the scenic towns surrounding the lake. Check out Varenna, Bellagio, and Menaggio, which offer great views, historic churches, and water-based activities such as ferries and passenger-only boats.

Varenna is a slow-paced destination—most visitors come here to relax by the lake. But even if "Working on my tan" is the #1 thing on your itinerary, take some time to explore the area. There’s the Castello di Vizio, a medieval fortress surrounded by an olive grove. And you’ll want to view the old, tiered gardens at the Villa Cipressi—they stretch all the way down to the water. Finally, visit the source of the Fiumelatte, a peculiar river—it’s only 250 m long and disappears from October to March.

A magnet for skiers and hikers, these dramatic peaks – including the iconic Matterhorn – range from 3,000 to 15,000 feet and spread across three-fifths of the country. Abundant glaciers, scenic valleys and gorgeous alpine lakes add to the region's visual appeal. The Glacier Express train travels the 7.5-hour route through the Swiss Alps from Zermatt to St. Moritz, passing through fairy-tale villages and over 291 bridges along the way.

Best known for its incredibly edible contributions to world gastronomy (especially parmigiano cheese and Parma ham), Parma has also been revered by opera lovers (who flock to its Teatro Regio) since the days of Verdi, who was born in nearby Roncole. Parma’s many historic sights include the 11th-century cathedral and its baptistry. Begun in the 12th century, it's considered one of medieval Europe’s most important buildings for its straddling of the Romanesque and Gothic architecture periods.

With its gondolas, canals, amazing restaurants, and unforgettable romantic ambiance, Venice is definitely a city for one's bucket list. Waterfront palazzos, palaces, and churches make drifting down the Grand Canal feel like cruising through a painting. To really experience Venice you must go to the opera or to a classical music performance, nibble fresh pasta and pastries, and linger in the exhibit halls of an art gallery. Label lovers will drool over the high-end shopping in Piazza San Marco.

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?

Everyone who visits Paris for the first time probably has the same punchlist of major attractions to hit: The Louvre, Notre Dame, The Eiffel Tower, etc. Just make sure you leave some time to wander the city’s grand boulevards and eat in as many cafes, bistros and brasseries as possible. And don’t forget the shopping—whether your tastes run to Louis Vuitton or Les Puces (the flea market), you can find it here.

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.

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.