One of Italy’s most visited regions, Veneto in the country’s northeast was independent for centuries until 1797, when Napoleon invaded. It then bounced among French, Austrian and Italian domination. Bordered by some of Europe’s most beautiful elements (the Adriatic Sea to its east, Lake Garda to its west, the Dolomites to its north, and the Po River to its south), Veneto is known for agriculturally rich valleys flowing down from Alps and for important cities like Venice, Verona and Padua.

Known as Padova in Italian, Padua may be the oldest city in northern Italy, if you believe the claims of its 12th-century BC founding by Trojans. It certainly has history, including its famous university (one of Europe’s oldest, from 1222), the 13th-century Basilica di Sant'Antonio (resting place of St. Anthony), and Scrovegni Chapel, with Giotto’s famed 14th century frescos. The magnificent Prato della Valle, a 950,000-square-foot elliptical square, is thought to be Europe’s second-biggest.

So splendid was mediaeval Verona that its reputation alone inspired Shakespeare to set two plays here (Romeo and Juliet and The Two Gentlemen of Verona). Though its connection to the actual Capulets is tenuous at best, the so-called Juliet's House draws half a million tourists per year, many of them keen on reenacting the balcony scene. Don't miss the Roman amphitheatre and the Palazzo Barberi.

With an enviable perch between the Adriatic Sea and Slovenia’s peaks, Trieste is an Italian city whose food, architecture, and history have Eastern soul. Add coastal castles to sun-soaked beach resorts, and you have one of Europe’s most cultured seaside getaways.

Trentino-Alto Adige is made up of two provinces, the Italian-leaning Trento (or Trentino) in the south and the Germanic-leaning Alto Adige (or Südtirol, and also called Bolzano-Bozen, just to keep things interesting) in the north. Home to numerous picturesque towns, castles and historic sights, the main attraction here is the mountains. The stars of these are the Dolomites. Outdoor adventure opportunities abound year-round, with skiing, climbing and hiking among the most popular pursuits.

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.

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.

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.