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.

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?

A cultural hub where elegant mosques and traditional bazaars dot the palm-lined boulevards and ancient Greek ruins look down from the hilltops, Turkey’s third-largest city, Izmir, has plenty to offer cruise visitors en route to nearby Ephesus.

About an hour south of Mombasa, the sparkling white sands and lush greenery of Diani invite you to relax under a beach umbrella with a refreshing drink. Try a camel ride for the tourist experience or book a bike tour inland for a glimpse of life in local villages. Diani is also a base for several safari companies.