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.

The “Red City” of Marrakesh is a magical place, brimming with markets, gardens, palaces, and mosques. Exploring the intimate courtyards and snaking alleyways of the historic Medina can easily eat up a day. Find inner peace at the serene Jardin Majorelle or take in the beauty of one of the city’s historic mosques (taking note that, unless you are Muslim, you are not allowed to enter).

Peschiera del Garda is located on the southern end of Lake Garda, in Italy's Veneto region. The town's sixteenth-century island fortress and walls are visible today, a reminder of a time when Austria controlled the region. After exploring Peschiera's history, relax with a glass of Lugana, a local white wine.