Synagogues, mosques and churches stand together in Toledo's historic quarter, a testament to the medieval Spanish city's diverse history. The four towers of The Alcazar, a fortress built in 1085, dominate the skyline. Toledo and its surrounding countryside inspired El Greco, and his paintings are on display in many places around the city, including the museum that bears his name.

Segovia is a picturesque old city with twisting alleyways, the highest concentration of Romanesque churches in all of Europe and pedestrian-only streets, all bordered by a medieval wall and two rivers. In 1985, this sleepy Castillan town was declared a World Heritage site by UNESCO. One of the main tourist attractions is Alcázar, a royal palace built sometime around the 11th century where Queen Isabel agreed to fund Christopher Columbus’ exploration of the New World. The picturesque palace is said to be Walt Disney’s inspiration for Cinderella's Castle.

Encircled by some of the best-preserved defense walls in Europe, ancient Avila seems straight from the Castile region's medieval past. Nighttime illumination only adds to the allure of the turrets, fortified palaces, and cathedrals of this storybook World Heritage city.

Castile-La Mancha, a Spanish land of craggy cliffs, golden fields and red soil, produces savoury Manchego cheese, olives, saffron and more than its share of mystery. Chase the enduring legend of Don Quixote among the windmills of Campo de Criptana. Pass through the Bisagra Gate to experience the walled city of Toledo, a UNESCO World Heritage site that pays stylistic tribute to the Christian, Jewish and Islamic cultures. In Guadalajara, palaces and Baroque churches capture the imagination.

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.

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?

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 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.

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.

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.

New Orleans is full of life—but with a laid-back energy that sets it apart from other cities. You’ll wanna soak it all in: impromptu jazz performances up and down Frenchmen Street, the ding of the St. Charles Streetcar, moss-draped trees in the famous Garden District…even its gothic, above-ground cemeteries. (The city’s said to be one of the most haunted in America.) For some, NOLA will always be all about Bourbon Street, but for travellers looking to take it slow, the city’s distinct blend of cultures—including Creole and Cajun—means there’s tons to see, explore, and yes, eat.