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.

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.

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.

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.

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?

Once known for smog, traffic and tacky architecture, Athens is a city reformed thanks to fortunes brought by the 2004 Summer Olympics. Spotless parks and streets, an ultra-modern metro, new motorways, an accessible airport and all signs in perfect English make the city easily negotiable. Meriting more than a stopover en route to the islands, sophisticated Athens sites include many pillars of Western history, from the Acropolis to the Temple of Olympian Zeus, as well as treasures in the National Archaeological Museum.

Over the centuries, many cultures have added their mark to this prized piece of land. Today, you can experience those influences firsthand by exploring Istanbul’s mahalles (neighbourhoods). From the holy sites of Sultanahmet and the 19th-century European elegance of Beyoğlu to the high fashion of Nişantaşı, the vibrant café society of Kadıköy and the football-loving streets of Beşiktaş, it’s easy to see why travellers say that Istanbul isn’t just one city, but many cities within one.

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.

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.