El Escorial 

Just an hour away from Madrid is the town of San Lorenzo de El Escorial, dominated by the vast palace-monastery built by Philip II. 

Declared a World Heritage Site by Unesco, El Escorial (pictured below) is one of Spain’s most beautiful Renaissance monuments and contains a wealth of artworks and the royal pantheon of tombs of Spanish monarchs.

The town is only an hour northwest of Madrid, easily accessible by the Cercanías train from Madrid’s Atocha station.

Valley of the Fallen

A short drive away from El Escorial is the imposing and controversial monument of General Francisco Franco, The Valle de los Caídos (Valley of the Fallen). The basilica hewn out of living rock by political prisoners of the dictatorship once contained the tomb of El Caudillo along with 40,000 people who died during the Spanish Civil War.

The site is marked by a giant memorial cross, visible for miles around but don’t expect to be informed about the Spanish Civil War or subsequent 36 year-old fascist dictatorship as no mention is made of its dark history.

Toledo

The charm of Toledo’s antiquated feel coupled with its winding cobblestone streets draws many visitors. Also a World Heritage Site, the city is a gorgeous medley of Christian, Muslim, and Jewish architecture.

Must-see sights include: The Castle of San Servando, the Alcázar fortress, El Greco Museum, the synagogues of El Transito and Santa María La Blanca, the Tornerías Mosque, the Roman Alcántara Bridge, and the Cathedral of Saint Mary. Aside from these, a relaxed stroll through Toledo’s streets is a must to truly appreciate its charm.

It is also famed for its regional cuisine. Toledo is only a 33-minute ride on the high-speed AVE train from Madrid’s Puerta de Atocha station. Tickets are as little as €13,90 and can be bought on the Renfe website.

Segovia

Segovia is another picturesque city appealing for its medieval charm. Like Toledo, a wander through its beautiful little alleyways, especially the Jewish Quarter, is an absolute must; so is a visit to the Plaza Mayor, the Alcázar, Segovia Cathedral, and the magnificent Roman Aqueduct dating back to the first century.

Don’t miss its fairytale castle, rumoured to be the inspiration behind Disney’s Cinderella’s castle. And no visit to Segovia would be complete without a taste of its famous roasted suckling pig. 

Segovia is 30 minutes by the high-speed AVE train from Madrid’s Chamartín station.

Ávila

Ávila boasts an extensive collection of Romanesque and Gothic churches, as well as impressively intact medieval-era walls encircling the city’s interior. The Gothic Cathedral and the Basílica de San Vicente are other popular attractions. Lose yourself wandering through the narrow alleyways discovering little plazas.

Ávila is a 1.5-hour ride on the high-speed AVE train from Madrid’s Chamartín station.

La Sierra de Guadarrama

This mountain range features stunning scenery, diverse flora and fauna, and numerous hiking trails. Situated between Ávila and Segovia, its hillsides include the Peñalara National Park, and the rock formations along the Manzanares River known as La Pedriza. The sierra is also a prime location for mountain sports, from ski-ing or snowshoeing in the winter to mountain biking and rock climbing.

The journey from Madrid to the Peñalara National Park involves two Cercanías trains. First, take the Cercanías to Cercedilla from Madrid’s Chamartín station (the ride is an hour and 20 minutes). Then take a 40-minute train from Cercedilla to Cotos, where one of the park’s three offices is located.

Cuenca

This fortress town has an old-fashioned appeal similar to some of the other places on the list, but it offers you a sight you won’t find just anywhere – the Hanging Houses perched atop the deep gorges of the Júcar and Huécar rivers. Cuenca also has a multicultural assortment of religious architecture, notably El Castillo (an Arab fortress) and the Cuenca Cathedral.

The high-speed AVE train takes 50 minutes from Madrid’s Atocha station to Cuenca.

Aranjuez

Another World Heritage Site, the beautiful town of Aranjuez served as a summer palace and hunting grounds for Royals of days gone by.  Its majestic architecture rivals that of the Royal Palace in Madrid and its magnificent gardens sprawling across 750 acres are worthy of an afternoon of exploration.

Aranjuez is a 45-minute train ride on the Cercanías via Madrid’s Atocha station but for a truly authentic experience then take the Strawberry Train, made up of restored wooden carriages from the early 20th century. During the hour-long journey, you can sample delicious strawberries grown in Aranjuez itself.

Chinchón

Chinchón is yet another addition to the towns on this list that you can’t miss simply for its charm. On your day here, visit the emblematic Plaza Mayor, famous for its irregular shape formed by medieval balconied houses.

Admire the view from the old clock tower, and buy titbits from its little artisan shops. It’s full of quirky events too, like the anisette liquor festival in spring and the garlic festival in autumn.

Chinchón is barely 45 minutes from Madrid by bus.

Alcalá de Henares

The cobbled streets give this city, along the river Henares, east of Madrid, a well-preserved medieval charm. The Gothic Cathedral and the Universidad Complutense – one of the world’s oldest universities – are popular attractions, along with a recently excavated site with a Roman basilica and public baths.

The Jewish, Moorish, and Christian quarters offer a delightful blend of architecture from different cultures.

The city is famed for being the birthplace of Miguel de Cervantes, author of Don Quixote.

Alcalá de Henares is 40 minutes from Madrid’s Atocha station on the Cercanías train.

Consuegra

If you’re a big fan of Cervantes’ work, head over to Consuegra next. The town has been famous since the 16th century for its windmills – the setting of a famous scene from Don Quixote where the knight errant battle with the sails he mistook for giants. Other sights include the Castle of Consuegra and the Renaissance-style town hall. 

Buses from Madrid to Consuegra make the trip in about two and a half hours, by car the trip is one hour and a half.