Map of Around Madrid

Madrid is a great base for exploring the centre of Spain. The map shows the most popular excursions, the towns of most interest within a short driving distance (under 1 h 35 min) of Madrid - they are by no means the only places worth visiting.

Easy Day-Trips
Toledo (90 km from Madrid, and connected by railway) is a fabulous mediaeval city with narrow, winding streets not unlike those you find in Morocco. It was once the "city of the three cultures," Christian, Jewish and Arabic, and its judería, Jewish quarter, is particularly notable. Its connections with El Greco make it unmissable for art lovers, it has one of the great Spanish cathedrals, and its Alcázar, now Spain's Army Museum, has an important place in Spanish military history.
Segovia (100 km from Madrid, and connected by railway) is also a mediaeval city, but has a different feel to it, more austere, more Castilian. Its most famous sight is its enormous Roman aqueduct, but wandering its streets is like stepping back to the times of the Reconquista, the Christian "reconquest" of Spain. Like Toledo, Segovia has one of the great Spanish Gothic cathedrals, and Segovia's Alcázar is also of great interest, with a fearsome history, in spite of being so picturesque it was the inspiration for Disney's famous "Sleeping Beauty" castle.
Ávila (120 km from Madrid, and connected by railway) is Spain's most mystical city, the home of Saint Theresa of Jesus, and yet another of the great cathedral cities of Spain. It is a world heritage site, though, for its amazing 11th-century city walls.
San Lorenzo de El Escorial (60 km from Madrid, and connected by cercanías, suburban railway) is a pleasant little town, interesting as a gateway to the Sierra de Madrid, but most notable as the site of the immensely imposing Royal Seat. This is half-palace and half-monastery, and was the nerve centre of the great Spanish Empire in the times of Philip II.
Aranjuez (50 km from Madrid, and connected by railway), in contrast, is a gorgeous riot of water and colour. Its royal palace is interesting enough, but its main attraction is the fabulous royal gardens, the inspiration for the famous Concierto de Aranjuez.
Chinchón (46 km from Madrid, not connected by railway) is a lovely little country town, with a splendid, ancient square where bullfights are still held and where Madrileños come at weekends to have lunch in one of its restaurants, specializing in Castilian roast meats (don't forget to try the local wine and the anis, anisette, made in the town, as well).
Alcalá de Henares (35 km from Madrid, and connected by cercanías, suburban railway) is one of the oldest university towns in Europe, and the first city ever to be specifically founded as a university, by Cardinal Cisneros in 1499. The (supposed) birthplace of Miguel Cervantes is visitable here as well
Near Segovia, the Royal Palace of La Granja de San Ildefonso (100 km from Madrid, not connected by railway and comfortably accessible by bus from Segovia, not Madrid) is also overshadowed by its own gardens, inspired by Versailles and famous for their fountains (La Granja is slightly inconvenient to visit unless you have wheels, though, so you may want to check that there are, for example, no water restrictions before you go).

For Explorers
Manzanares el Real (42 km from Madrid, not connected by railway) is a fine country town with a brilliant castle, and though near the capital is a little out of the way, so best visited while touring the north of the province of Madrid, especially the Sierra Norte to which it is a gateway. North-east and east, respectively, of Guadalajara, the tiny, once noble cities of Brihuega and Pastrana mark the northern and (roughly) southern limits of the fascinating Alcarría region. And, further on, historic Sigüenza (130 km from Madrid, well connected by railway), in the north of New Castile, though well communicated with Madrid, is also normally visited on the move, preferably with an overnight stay in its splendid parador, one of the best in the country, a restored castle. If you can't afford to stay there, stop in for a coffee or a beer, or even a meal.