This article covers Toledo, Segovia, El Escorial, and Alcalá de Henares. Each of them can easily be visited on a day trip from Madrid, each of them is a UNESCO World Heritage site, and at least the first two can sustain a longer stay for those inclined to more in-depth exploration.
Toledo
Toledo ♥♥♥ is such a beautiful and full-of-history destination that it certainly warrants more than an intraday trip from Madrid. The medieval melting pot of Christian, Muslim, and Jewish cultures, Toledo was for a time one of the most important cities in all of Europe. Its historic center, dramatically sitting behind old walls high on a hill above the River Tagus, offers a lot of the city’s rich history on display.
The most remarkable sight in Toledo is its massive Cathedral ♥♥♥. Its interior is nothing short of splendid, full of decorations and artifacts, with several pipe organs built in different styles. Brilliant stained-glass windows and frescoes are present throughout the cathedral. In the choir, every seat is marked with a unique carved sculpture. In the cardinal picture gallery, there are two portraits by Goya that always get a dismissive reaction from the tourists when compared to more “realistic” other portraits painted by less-known artists.
Monasterio de San Juan de Los Reyes ♥♥♥ boasts beautiful cloisters and a great church.
The ancient mezquita San Christi de Luz ♥ is another point of interest. For an elevated view of the city’s roofline, climb the tower of the Church of Jesuits ♥. Quite a few other churches are worth a look.
In the Jewish Quarter, Sinagoga de Santa María la Blanca ♥♥, the oldest and largest of the city’s eight original synagogues, is now restored to its maiden beauty, with its Mudejar columns and remains of Catholic frescoes. Another temple, Sinagoga del Tránsito ♥♥, impresses with its main prayer hall with a high ceiling, but it is also a great museum of Jewish history and customs. Several rooms have various objects on display, accompanied by good tour booklets in various languages.
As you walk around the Quarter, look for the pavement marker insets. They helped the local community function and find security.
The painter El Greco spent the second half of his life in Toledo, and there are a number of his works in various city churches and museums, as well as a dedicated Casa-Museo de El Greco (which supposedly has none of his works). Iglesia de Santo Tomé displays one of El Greco’s masterpieces, The Burial of the Count of Orgaz.
Museo de Santa Cruz is the most prominent art collection in town. The grand building of Alcázar can be seen from a number of vantage points in town. It is nowadays the main military museum in Spain. Toledo is a suitable place for a museum of arms. Its souvenir shops are full of swords, knives, and such. I don’t know anyone who comes back from a visit to Toledo without at least a picture of themselves wielding a heavy sword; some return with the actual weaponry.
A couple of other museums worth considering are Museo Taller del Moro and Museo del Queso Manchego.
San Martin’s Bridge is reputedly the most picturesque river crossing underneath the town.
Transportation
If traveling to Toledo by train, keep in mind that the station is located not too close to the historic center. It is technically within walkable limits – about half an hour – and allows for great views over the river that you probably cannot get if traveling by taxi or bus, but most people will likely need the use of the transport.
Segovia
Segovia is breathtakingly pretty and very easy to fall in love with. There are not too many attractions that specifically merit a visit, but walking the streets of the historic town core is a treat, with many houses decorated with elaborate ornamental stucco patterns. There are also numerous artisanal shops to browse, many pretty squares to rest at, and amazing vistas all over the place.
The 2000-year-old Aqueduct ♥♥♥ meets you as you enter the city center and bids you farewell when you leave. The amazing structure was in use until the 19th century and remains in pretty good shape nowadays. You cannot climb on its top, but you can walk up the stairs on the side of Plaza del Azoguejo to get a nearly level view of the Aqueduct’s upper tier.
The aqueduct continues underground across the city, and you can follow its route above by walking along commemorative plaques that mark its location in two dozen places.
Segovia’s Cathedral ♥♥♥ may not be as famous as Toledo’s, but it is the last-built great Gothic church in Spain. Its many chapels are accessible to the visitors (as is often not the case elsewhere), so there is plenty of exploring to be had. Near the Cloisters, there is the fine Sala Capitulares and a small museum.
Alcázar ♥♥♥ is another unmissable sight. Not only there are magnificent views of the Castilian countryside from its walls and the Tower (152 steps to climb up), but also there are a series of elaborately decorated rooms inside (don’t forget to look up to check the luxurious ceilings – each room is vying to be the most luxurious), and the castle has a quintessential fairy-tale look and feel. Since it is located some kilometer or so away from the center of Segovia, you can also see the panoramic view of the town, dominated by the cathedral, from the same Tower.
There are also several churches and monasteries in town, and a fine arts museum or two, but they only can fit into a visit if you stay more than a day. Which is entirely warranted.
Transportation
If traveling to Segovia by train, keep in mind that the station is not within walking distance from the historic center. Taxis or buses are plentiful.
When you are riding back to the train station, ask the driver to point out to you Mujer Muerta, a mountain massif that looks like a woman lying on her deathbed. Rather eerie.
San Lorenzo de El Escorial
The imposing grey palace of El Escorial ♥♥♥ is a great destination for half a day away from Madrid. The unornamentally severe palace was intended to serve as a mausoleum and a contemplative retreat, rather than an opulent country residence. The royal apartments are quite humble, but the main attractions of the palace are its artistic wealth and the splendor of some of its main purposed rooms, especially the Library, which holds forty thousand books in twelve languages, the Basílica, with a lavish altarpiece, the Royal Pantheon, with the funerary urns of Spanish monarchs, and Sala de Batallas, the walls and the ceiling of which are covered in paintings depicting various battles. The Museum of Art on-site contains a number of Flemish, Italian, and Spanish paintings.
The palace is huge, and touring it with an audio guide takes around three hours at a minimum. The village, over which the complex towers, is conversely rather nondescript.
Transportation
If traveling by train, keep in mind that the station is located some distance downhill from the palace; I recommend taking the municipal bus uphill and leaving the walking bit for the return leg of the trip.
Alcalá de Henares
Alcalá de Henares ♥ is a pretty university town that also happens to be the birthplace of a certain Miguel de Cervantes Saavedra. The historic center of the city converges on Cervantes Plaza ♥ and stretches along Calle Mayor ♥, which is headlined by the ever-popular statue of Don Quixote and Sancho Pansa ♥ sitting on a bench.
You can walk through the courtyards of the university ♥, but interior access is allowed only with a guided tour in Spanish. A similar tour is available separately for Capilla de San Ildefonso ♥ where viewing a single space makes it less problematic not being able to understand the commentary (in a lucky twist, I was the only person interested in the tour at the scheduled time and the guide spoke passing English and was nice enough to indulge me).
The Magisterial Cathedral ♥ is worth a visit if not truly exceptional.
Among the places worth considering seeing in Alcalá de Henares are the Cervantes House/Museum, the historic Corral de Comedias, the Archbishop’s Palace, and the regional Archaeology Museum.
If you walk to the edge of town, you can see Puerta de Madrid – a counterpart to Puerta de Alcalá in the capital. They guard roads that lead to each other, hence the names.
Transportation
Traveling by train is relatively easy from Madrid, as the station is well within walking distance from the center of town.