This capital of Spain offers the culture and appeal of a sophisticated modern city, while retaining the charm and elegance of its early years. Upon arrival, pick up your rental car and make your way to your hotel and home for the next five nights.  From here you’re free to begin exploring the city! Among the splendid attractions of Madrid are the Prado Museum, home to masterworks of Goya, Velazquez and El Greco; the 19th century Villahermosa Palace, now the Thyssen-Bornemizsa Museum; the Reina Sofia Art Centre, showcasing more than 300 modern works by Dali, Miro and Picasso among others; the 18th century Royal Palace, situated on the lovely Plaza de Oriente; the bustling Puerta del Sol with its many shops, restaurants and tapas bars; Rastro Market on Sundays, one of the oldest outdoor markets in Europe; and Retiro Park for strolling while admiring local artists. 

Following breakfast, set out for Toledo – approximately 45 miles southeast of, and one hour from your hotel. This marvelous city enjoys a picturesque location upon a hill – and behind its medieval walls lies much evidence of its rich history. In the Middle Ages Christian, Muslim and Jewish cultures lived side by side here, and it was during the same period that the Cathedral, the city’s most outstanding monument, was built. The Mudejar Art style is well represented in Toledo and two of the best examples are the synagogues of Santa Maria La Blanca and El Transito. The latter, of the late 12th century, embodies an exotic influence and mixture of arts. The former, of the 14th century, has one of the best coffered ceilings in Toledo. Other interesting places to visit are the Taller del Moro (Moor’s Workshop) and The Cristo de la Luz (Christ’s Light).

Today, you should head to the medieval city of Avila, 70 miles northwest of your hotel, and approximately 75 to 90 minutes away. Sheltered by the Sierra Gredos Mountains, the Old Town of Avila has been a World Heritage City since 1985. Avila’s medieval walls protect an incredible wealth of history and heritage – with a valuable set of churches and Renaissance palaces that bear witness to the past wealth of the town as a textile center. Don’t miss the Cathedral (dating back to the 11th century) and its museum, and the 17th century Santa Teresa Convent – as well as the rich local cuisine made up of excellent roasts and the famous Avila veal cutlet!

From Avila, travel 40 miles east to the World Heritage City of Segovia, which lies on high ground between the Eresma and Clamores Rivers. Its buildings speak of times long past, with numerous Romanesque churches, the Cathedral and Fortress forming a magnificent landscape. Segovia’s magnificent Roman Aqueduct (also a World Heritage Site), recalls the immense power and reach of the Roman Empire.

From Madrid, drive approximately 35 miles northwest (45 minutes) to El Escorial. This spectacular monastery-palace stands in the heart of the Guadarrama Mountains, and was built between 1563 and 1584, in honor of St. Lawrence (San Lorenzo). Its artistic wealth includes important works of the royal Habsburg collections and over 40,000 books in the library, with ceilings decorated with frescoes by Tibaldi. Of special interest are the Royal Pantheon and the Museum of Art.

After breakfast, make your way to the magical, medieval fortified city of Cuenca – located approximately 105 miles southeast of Madrid (estimated driving time is 1.5 – 2 hours). This UNESCO World Heritage Site lies between Júcar and Huécar river canyons – and it will charm you with its cobbled streets, incredible Hanging Houses (Casas Colgadas), Cathedral, San Miguel Church, San Pedro Church, Descalzas Convent and San Nicolas. Discover the beauty of the nearby Enchanted City (Ciudad Encantada), where stone comes to life. The Museum of Abstract Art will appeal greatly to art lovers. And for the curious of mind, what better than a visit to the Castile-La Mancha Museum of Sciences and the provincial archaeological museum.

Following breakfast (or depending on the time of your return flight), make your way back to the airport and return your rental car, in preparation for your journey home.