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 Cuenca - 103 miles - 2 hours)

Day 2:  Cuenca
The Eagles` Nest
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?
(Cuenca to Alcala de Henares -111 miles - 2 hours)

Day 3:  Alcala de Henares
The cradle of Cervantes
This town near Madrid, birthplace of the illustrious Miguel de Cervantes, author of "Don Quixote", and home to one of the most prestigious universities in Spain, has been declared a World Heritage Site by UNESCO. Its rich monumental heritage, formed by churches, convents and university buildings, gives us a glimpse of life in Castille during the Spanish Golden Age. Its historic quarter also has the "Mesón del Estudiante" Inn, which is part of the network of Paradores de Turismo. Walls with four hundred years of history make the perfect place to sample the best of the local gastronomy. A stroll down the bustling high street, where Cervantes was born, marks the beginning of a tour of the city that takes in its university, St. María La Mayor, the streets of St. Úrsula and Los Escritorios, and much more. A perfect backdrop against which to enjoy the Alcalá Classic Theatre Festival in the summer.
(Alcala de Henares to Segovia -80 miles - 1 hour and 40 minutes)

Day 4:  Segovia
Bastion of Rome
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.
(Segovia to Avila - 53 miles - 1 hour)

Day 5:  Avila
The Soul of St. Teresa
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 Salamanca - 60 miles - 1 hour and 20 minutes)

Day 6:  Salamanca
Spain`s Oldest University
Salamanca provides a feast of art and architecture to finish the route with, a city where the hustle and bustle of University life has gone undisturbed since the 16th century. Salmántica belonged to the Roman province of Lusitania, was besieged by Hannibal, conquered by the Arabs, lost and recuperated several times by the Christians, and definitively reconquered by the great pro-European king Alfonso VI.  Pre-Roman remains can be found in Teso de San Vicente, beside the river Tormes, in the Verraco (Iberian statue representing a bull) situated in the centre of the Roman Bridge, in the city walls, in numerous inscriptions and along the Calzada de la Plata. In 1200 Alfonso IX founded what was to become eighteen years later the University of Salamanca. Salamanca is a city of the golden glow.  Luscious hues of ever- changing honey and copper reflect off the sandstone walls of Spain's oldest university and numerous churches.  The Plaza Mayor and the Casa de las Conchas (house of conch shells), the Plaza de Anaya - all gather and return the wondrous play of light in this splendid city. The congruency and perfect "fit" of its stone architecture creates a beauty unsurpassed in any other city in Spain. 
(Salamanca to Madrid - 130 miles - 2 hours and 40 minutes)

Day 7:  Madrid
Spend your last day enjoying Madrid.