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.

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.

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.

Getting to hilltop Orvieto is half the fun, with the choice of ascending by escalator or funicular cable car. The strategically built old town is free from modern-day traffic, inviting visitors to enjoy a taste of medieval Umbria—and a glass of famous Orvieto Classico wine.

Sitting where the Phoenician colony of Hadrumetum once stood nearly 3,000 years ago, the modern-day Sousse is a resort destination, especially popular with Europeans. Sometimes called "the Pearl of the Sahel" (referring to the central section of Tunisia's eastern shoreline), Sousse is prized for its excellent beaches. Arab-Islamic since the 7th century AD, the city has many fascinating attractions, like the 9th-century Great Mosque, and its medina is a UNESCO World Heritage Site.

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?

Known as Padova in Italian, Padua may be the oldest city in northern Italy, if you believe the claims of its 12th-century BC founding by Trojans. It certainly has history, including its famous university (one of Europe’s oldest, from 1222), the 13th-century Basilica di Sant'Antonio (resting place of St. Anthony), and Scrovegni Chapel, with Giotto’s famed 14th century frescos. The magnificent Prato della Valle, a 950,000-square-foot elliptical square, is thought to be Europe’s second-biggest.

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.

Known as the safari capital of Africa, Nairobi is an energetic, modern city that serves as a fascinating introduction to both wildlife and nightlife. Music clubs pulse with life, shops and markets bustle, and a mélange of restaurants will tempt your palate in this former Maasai watering hole. Top sights include the Karen Blixen Museum, Giraffe Centre and the black rhinos of Nairobi National Park. The compact city centre is safe to walk in and taxis make other areas accessible.