One of the most popular regions in Italy, Tuscany stretches from the Tyrrhenian Sea to the Apennines. Its main cities include Florence, Pisa, Siena, Lucca, Arezzo and Livorno. Drive between stunning sites like Florence's cathedral and Uffizi Gallery and the Leaning Tower of Pisa. Or join a bike tour and pedal past sun-baked olive groves and vineyards. Don't miss the towers of San Gimignano or serene northern hill towns. For a more modern take, hit one of Florence's hip clubs, such as Space Electronic.

This Tuscan hill town will transport you back to the Middle Ages. Siena's grand cathedral, built in the 1200s, has treasured artworks and marvellous marble floors. The Piazza del Campo, the main town square, is a UNESCO World Heritage Site. It's also home to the Palio, perhaps the most infamous horserace in the world. No goofy hats and mint juleps here—this is a mediaeval tradition involving bareback riders racing on cobblestones (so as you might imagine, it's quite dangerous). Siena is an easy daytrip by train from Florence, just 43 miles away.

Lucca's array of wonderfully intact historical sites makes it a must-see stop on any Tuscan itinerary. The mediaeval city walls still stand—you can hike or bike on top of them. Also visit the Duomo di San Martino and the Roman amphitheatre.

About a 25-mile drive southeast of Siena in the rolling hills of Tuscany’s Crete Senesi region, San Giovanni d'Asso is home to just a few hundred people. The highlight is the 12th-century castle, which now houses town offices. Directly opposite the castle is Villa San Giovanni, complete with a hanging garden, which is rentable by the week. The town is home to two lovely old churches, San Giovanni Battista and San Pietro in Villore. Every November, San Giovanni d'Asso holds a Truffle Festival.

While crowds of tourists fill Venice, Florence and Rome, Bologna remains relatively quiet in comparison. This mediaeval university town is charming, historic and fun to explore… and you'll find Bologna's local cuisine is light-years away from the American deli meat bearing the city's name.

Centrally located Umbria's principal cities include Spoleto, Assisi, and Terni. The capital, Perugia, is famed for its chocolate. Take a tour bus or prepare for daredevil Italian drivers if you opt to rent a car. Assisi's Basilica has a host of treasures, including works by Giotto. The town is also home to the crypt of St. Clare, patron saint of television. St. Francis' meditation retreat is in the mountains to the north. Classes at Velia's Cooking Style in Terni make good use of local produce.

Often an overnight stop en route to Cinque Terre, La Spezia offers travellers more than just affordable stays. Beyond a working-class port and naval base, there are maritime and archaeological museums, a hilltop castle, and an old town ideal for exploring and sampling Ligurian cuisine.

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.

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.

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!

travellers say Halifax is best seen on foot, so park the car and start walking. Immerse yourself in Halifax's rich history at the Maritime Museum of the Atlantic, and be sure to survey the city from the 18th-century Citadel National Historic Site. Then walk into any of Halifax's great bars and restaurants and catch some live music to round out your day.

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.

You've got to walk the Freedom Trail the first time you visit Boston. That's just a given. Make sure you step off the line on the pavement, though, and explore some of Boston's fine museums (try the Gardner—art masterpieces displayed in their collector's mansion) and old neighbourhoods (like the North End, where you can get the best cannoli this side of Italy). You can't claim to have experienced real Boston culture, though, unless you've watched a Red Sox game from the bleachers.

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.

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.