Following is our suggested itinerary, please note that you may extend the number of nights in each city:
Day 1: Madrid
Madrid is a city of great contrast and tendencies that provide a feast for the eyes: the Old City, the innumerable churches and convents, the Madrid of the Hapsburgs, the Royal Palace, the Puerta de Alcala, the Retiro Park, etc. Every façade, corner, statue or park has its own particular charm. It`s museum mile offers more masterpieces per square foot than anywhere else in the world; the stellar Prado with its El Grecos and Velazquezes; the Caravaggios and Rembrandts at the Thyssen-Bornemisza; and the Dalís, Mirós and Picasso's wrenching Guernica, at the Reina Sofía.
(Madrid to Segovia - 60 miles - 1 hour and 15 minutes)
Day 2: Segovia
If its Aqueduct is Ancient Rome, its cathedral, fortress and churches evoke the Middle Ages, the Renaissance and Baroque. With its Alcazar and Roman aqueduct, it is one of the most interesting and visually pleasing of cities. Standing and gazing out from the world-renown castle, one is transported to some vaguely-recalled fairytale. Everything about Segovia is mesmerizing and photogenic. With each turn, you'll be confronted with another picture-worthy vista - be sure and wander with camera at the ready! The Romans were here over 2000 years ago - the Visigoths and Arabs followed. They've all left their marks and helped create a fascinating city in a stunning setting. The entrance gate to the historic quarter of Segovia is the Roman Aqueduct, in the plaza del Azoguejo. This jewel of engineering, built under the Roman Empire (1st c.), brought water to the high city from 15 kilometers away. Its 163 arches and 29 meters at its highest point are supported by blocks of stone from the Sierra de Guadarrama without mortar, lead or cement. The Parador enjoys a privileged view across this city, which oozes history. Round this off by sampling the popular roast meats and don`t forget to visit the Royal Palace of La Granja de San Ildefonso.
The modern Parador Segovia is called the "viewpoint of Segovia" - Its views out over the city are panoramic. All rooms have "postcard" vistas. As usual, the restaurant serves delicious Castilian cuisine.
(Segovia to Avila - 53 miles - 1 hour)
Day 3: Avila
The extensive history of Avila begins with the primitive Celtiberian settlement of the Vetones around 700 B.C. The first wall was built with the arrival of the Romans in the third century B.C., making Avila a strategic point of defense. The wall is the symbol of the city and it is one of the best kept, medieval walled enclosures in Europe. Its two and a half kilometer perimeter is marked by almost 2,500 crenellations, a hundred towers, six gates and three openings. Throughout history, Avila was the birthplace of famous Spanish mystics, like Santa Teresa de Jesús and San Juan de la Cruz. Visiting the cathedral, the Convent of St. Teresa, the palaces is simply a must, as is sampling the big beans at the El Barco village and the St. Teresa candies. Avila rests in stately slumber behind perfectly preserved medieval walls. It's almost as if time has passed her by.
In the historic old quarter of Ávila you will find the Parador, which is built right up against the city walls, which in turn become theatrical stages during summer?s night. The Parador is a former 16th century palace with granite floors and large bright rooms. It has pleasant gardens, and the restaurant serves the delicious specialties of Castile in a large stone and wood dining room. All together - you are assured of a memorable stay.
(Avila to Toledo - 116 miles - 2 hours)
Day 4 and 5: Toledo
Toledo is one of the Spanish cities with the greatest wealth of monuments. Known as the ?city of the three cultures?, because Christians, Arabs and Jews lived together there for centuries, behind its walls Toledo preserves an artistic and cultural legacy in the form of churches, palaces, fortresses, mosques and synagogues. This great diversity of artistic styles makes the old quarter of the capital of La Mancha a real open-air museum, which has led to it being declared a World Heritage Site. For many, Toledo mesmerizes - it exudes a strangely powerful attraction - dark, claustrophobic and profound. It was the seat of the Spanish Inquisition, the home of the brilliantly disturbed El Greco, and the scene of both vicious and heroic events during the Spanish civil war. It is architecturally and culturally fascinating like few other cities could be. To look at Toledo from afar, is to be beguiled and astonished.
The Parador Toledo is on a remarkable site that has unmatched views out over the city. The building was originally built by the Count of Toledo in the 14th century and is completely Toledan in character. The restaurant serves as a school for the chefs of the other paradors, and the meals are nothing short of spectacular.
(Toledo to Chinchon - 43 miles - 1 hour and 15 minutes)
Day 6: Chinchon
Chinchón is recognizable in the distance by its houses clustered together on hilltops. The beautiful medieval square is Chinchón's most emblematic landmark. Irregular in shape and formed by houses of two and three floors with running balconies, it has been the scene of a great many events and presentations. As well as its characteristic Plaza Mayor, with its wooden balconies and flat galleries, there is also the church of Nuestra Señora de la Asunción (1534-1626), which was sacked and burned by Napoleonic troops in 1808. Inside is the magnificent painting of La Asunción de la Virgen, painted by Goya. Prominent in the town centre are the nobles' mansions with their coats of arms and ancestral homes with beautiful courtyards and galleries resting on Doric, Ionic and Tuscan columns or with bases of stone. Chinchon is a little-known gem of a town. The laid-back atmosphere of the unique main plaza conjures up images of what Spain must have been like a hundred years ago. Chinchon is also famous for its anise liqueur which you can purchase at any of the little market nooks around the plaza.
The Parador Chinchon is perfect for the traveler who wants to relax in tranquility. This Parador is a converted 17th century Augustinian Convent that is situated a few yards from the Plaza Mayor in the heart of the old quarter. It has beautiful private gardens and an original cloister that contribute to it's ambience of peace and quiet.
(Chinchon to Cuenca - 81 miles - 1 hour and 30 minutes)
Day 7: Cuenca
Cuenca?s old town has the UNESCO World Heritage designation, and the city spreads out from atop a promontory overlooking the ruins of its Moorish castle, the ancient Kunka fortress. It sits serenely between the gorges formed by the Júcar and Huécar rivers. Cuenca is a magical city with its Hanging Houses from the 15th century, San Miguel Cathedral church and San Pedro Church, the Convent of the Descalzas and San Nicolás, among other monuments. Discover the beauty of the nearby Ciudad Encantada (Enchanted City), where the stone comes to life. The Museum of Abstract Art opens its doors to art lovers and for the curious of mind, what better spots than the Castile-La Mancha Museum of Sciences and the provincial Archeological Museum
Night time strolling through the city's old quarter has a special appeal - as does hiking along the river below the city and gazing back up at the soaring, venerable "skyscrapers" of Cuenca. A drive out to Ciudad Encantada will make for a fun half-day trip. The fantastical rock formations there are fascinating. Walk the pleasant trails that wander through them - take a picnic lunch and enjoy the incredible surroundings.
The elegant Parador Cuenca is a converted 16th century convent. Many of the rooms have breathtaking direct views across to the famous "hanging houses," others overlook the river far below. Frescos and ornate plasterwork are everywhere, and a soothing garden now fills the original cloister. There is an incredible foot-bridge that connects the Parador with the hanging houses section across the gorge. This 4 star hotel assures a remarkable experience.
(Cuenca to Siguenza - 109 miles - 2 hours and 30 minutes)
Day 8: Siguenza
When you arrive in the city, you cannot help but be amazed by the beauty it displays. Its lofty architectural heritage was declared a Historic-Artistic Site in 1965. The castle, the cathedral, and the main square, or Plaza Mayor, are three spots that the visitor should not miss in the city, although most streets in Sigüenza are filled with gorgeous civil and religious buildings. At present, the castle houses the town's Parador de Turismo. It was built after the Arab invasion in the 8th century, around the same time that the Alcazaba (citadel) was built. Significant parts of the wall are preserved, whose gates and towers begin at the castle. The cathedral, started in 1130, is Romanesque, although it was finished following Gothic canons. Its exterior resembles a medieval fortress, and has Romanesque towers and portico, as well as an impressive rose window. Other highlights include the Main Square, the House of the Doncel, the façade of the Clarisas de Santiago, San Vicente Parish Church and Sta. María Parish Church. Squares and streets to discover, to explore, to travel back to a splendorous past!
The Parador Siguenza occupies a massive castle whose construction was begun in 1123 A.D.. Through the centuries, it has served as a residence to bishops, cardinals and monarchs. Today it will provide you with all the modern comforts while still maintaining its air of antiquity. One of the finest and most historically interesting in the Parador chain.
(Siguenza to Madrid - 81 miles - 1 hour and 40 minutes)
Day 9: Madrid
Spend your last day in Madrid.