Milan is the prime draw in Italy's most prosperous province. The Cathedral, La Scala opera house and Santa Maria delle Grazie, home of da Vinci's Last Supper, are just some of the sights. Equally fascinating is the belle poque splendor of 19th-century Galleria Vittorio Emanuele II. When not on one of its frequent strikes, Milan's Metro is an excellent way to explore. Renting a car opens up the region, with its towns full of Romanesque architecture and the peninsula of Sirmione and Gardesana coast.

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.

On the south side of the Alps, Lake Maggiore is the second largest lake in Italy. Since the climate is mild year-round, the area is filled with Mediterranean vegetation and exotic plants. Lake Maggiore was featured in Ernest Hemingway's infamous novel, A Farewell to Arms, when the protagonist and his lover must row across the lake in order to escape the Italian Carabinieri (think police in military uniforms). Here's hoping you won't have any run-ins of that nature.

Lake Maggiore—one of the largest lakes in Italy—is known for its Alpine splendor, and the resort town of Stresa is a perfectly elegant place to admire its beauty. A quick trip from Milan, the town features opulent villas, pretty piazzas, and the storied Grand Hotel.

One in a constellation of elegant resort towns ringing Lake Garda (Italy’s largest lake), the southerly Desenzano Del Garda is celebrated for its Roman villa, castle, and archaeological museum. It’s just a quick trip from larger hubs like Brescia and Verona, too.

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.

You’ll find vineyards and olive groves in Bardolino, as well as beaches on beautiful Lake Garda. This town isn’t as popular as other area resort towns, so you shouldn’t find huge crowds here (except perhaps during the local olive oil and wine festival in late September and October). If you’re travelling with kids, make a beeline for the Gardaland and Aqua Paradise amusement parks.

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.

We hear the question, "What’s the next Prague?" a lot. But while we’re all for discovering great new destinations, we hardly think Prague is over. Sure, everyone’s heard of it, but it’s still a grand city with extraordinary historic and cultural sights, and it’s definitely worth a visit. The often-rebuilt Prague Castle has overlooked the city since the 9th century, and the synagogues and cemetery of the Jewish Quarter are must-sees. Nightlife here is diverse and plentiful, from trendy clubs to sophisticated wine bars to late-night cellar bars.

Stroll Las Ramblas and enjoy Barcelona's unique blend of Catalan culture, distinctive architecture, lively nightlife and trendy, stylish hotels. You'll find Europe's best-preserved Gothic Quarter here, as well as amazing architectural works by Gaudi. La Sagrada Familia, considered Gaudi's masterpiece, is still under construction (your entrance fee helps to fund the project). Feel like a picnic? Look no further than the rambunctious La Boqueria market, where you can stock up on local delicacies.

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.

Lisbon, the capital city of Portugal, has become an increasingly popular place to visit in recent years, with a warm Mediterranean climate in spite of its place facing the Atlantic Ocean. Full of bleached white limestone buildings and intimate alleyways, Lisbon's mix of traditional architecture and contemporary culture makes it the perfect place for a family holiday. Things to do in Lisbon: As Portugal's capital, there is a lot to see and do in Lisbon. Even exploring the city centre will take a few days out of a family holiday as there is no real central district, although Praça do Comércio is a good central place to start, in Baxia, or Rossio, the city's main square which has a sort of Trafalgar Square feel to it. Or you might try climbing up the Cristo Rei, a huge statue of Christ with spectacular views across the whole city. The Castelo de São Jorge also offers great views and isn't quite such a steep climb. A short tram ride to the west of Lisbon will also bring you to Belem, where you can explore attractions like the Belem Tower and the Belem Cultural Centre, which features a fantastic art collection including works by Dali, Picasso, Warhol and Magritte. In downtown Lisbon, you'll also want to visit the Gulbenkian, which has to be Portugal's answer to the British Museum full of fascinating cultural artifacts and with some superb gardens in the grounds. It's possible to have a fascinating educational family holiday in Lisbon, and there are also plenty of great beaches to work on your tan.

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.

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.

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.