Galas, regattas, the Film Festival and an outrageously attractive and affluent set characterize Cannes. Vast yachts obscure the view and the town lives up to its motto, "Life is a festival." People-watching is the activity that brings most visitors to Cannes, and hotel-lined La Croisette provides a fine promenade. First popularized by Coco Chanel, Cannes beaches are a huge draw. Get expensive seaside food and drinks service on hotel sand or opt for the free public beaches, Plages du Midi and de la Boca.

Known as the City of Palms, scenic seaside Bordighera is the proud supplier of fronds to the Vatican every Palm Sunday. Just a few miles from the borders of both Monaco and France, floral Bordighera has been a favorite resort destination for British visitors since the 19th century, when Queen Victoria herself was a guest. The town has many lovely gardens (like Pallanca and Winter), an archaeological museum (the Bicknell) and a lovely old town, but most come for the beach and seafront promenade.

With seemingly endless sunny beaches, charming towns, glamorous yachts and celebrities galore, the French Riviera keeps the Belle Époque alive. Most towns are best explored on foot, while a cheap and reliable rail network connects the cities and towns. Fabled destinations such as St-Tropez, Nice, Cannes, Antibes, Villefranche-sur-Mer and St-Jean-Cap-Ferrat lure visitors to follow in the wake of Picasso, Matisse and Bizet. Over a hundred museums and more than 150 galleries keep the artistic ambiance alive.

As the oldest resort town on the French Riviera, Hyeres has been entertaining France’s aristocracy for centuries, and its medieval old town—perched on a hilltop overlooking the coastal islands and salt marshes—maintains an air of elegance.

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.