Charles V’s fortified palace stands on the site of former Roman, Visigothic and Muslim fortresses. Its severe square profile suffered damage by fire three times before being almost completely destroyed in 1936 when the Nationalists survived a 70-day siege by the Republicans. Restoration followed the original plans and the siege headquarters have been preserved as a monument to Nationalist heroism. The former National Museo del Ejército was transferred from Madrid to this building, making the Alcázar the main army museum in Spain.

The Borbón-Lorenzana Library (open to the public) contains 100,000 books and manuscripts from the 16th to 19th centuries.

This museum is housed in a 16th-century hospital founded by Cardinal Mendoza. The building has some outstanding Renaissance architectural features, including the main doorway, staircase and cloister. The four main wings, laid out in the shape of a Greek cross, are dedicated to the fine arts. The collection is especially strong in medieval and Renaissance tapestries, paintings and sculptures. There are also works by El Greco, including one of his last paintings, The Assumption  (1613), still in its original altarpiece. Decorative arts on display include two typically Toledan crafts: armour and damascened swords, made by inlaying blackened steel with gold wire. Damascene work, such as plates and jewellery (as well as swords), is still produced in the city.

Visitors come to Santo Tomé mainly to admire El Greco’s masterpiece, The Burial of the Count of Orgaz . The Count paid for much of the 14th-century building that stands today. The painting, commissioned in his memory by a parish priest, depicts the miraculous appearance of St Augustine and St Stephen at his burial, to raise his body to heaven. It has never been moved from the setting for which it was painted, nor restored. Nevertheless, it is remarkable for its contrast of glowing and sombre colours. In the foreground, allegedly, are the artist and his son (both looking out) as well as Cervates. The church is thought to date back to the 11th century, and its tower is a fine example of Mudéjar architecture.

Nearby is the Pastelería Santo Tomé , a good place to buy locally made marzipan.

The oldest and largest of the city’s original synagogues, this monument dates back to the 12–13th century. In 1405 it was taken over as a church by San Vincente Ferrer after the expulsion of the Jews. Restoration has returned it to its original beauty – carved stone capitals and wall panels stand out against white horse-shoe arches and plaster-work. In the main chapel is a Plater-esque altarpiece. In 1391 a massacre of Jews took place on this site, a turning point after years of religious tolerance in the city.

The most elaborate Mudéjar interior in the city is hidden behind the deceptively humble façade of this former synagogue, built in the 14th century by Samuel Ha-Leví, the Jewish treasurer to Pedro the Cruel. The interlaced frieze of the lofty prayer hall harmoniously fuses Islamic, Gothic and Hebrew geometric motifs below a wonderful coffered ceiling.

The synagogue houses a museum of Sephardi (Spanish Jewish) culture. The items on display date from both before and after the Jews’ expulsion from Spain in the late 15th century.

A wonderful mixture of architectural styles, this monastery was commissioned by the Catholic Monarchs in honour of their victory at the battle of Toro in 1476. It was originally intended to be their burial place, but they were actually laid to rest in Granada. Largely the work of Juan Guas, the church’s main Isabelline structure was completed in 1496. Although it was badly damaged by Napoleon’s troops in 1808, it has been restored to its original splendour with features such as a Gothic cloister (1510) which has a multicoloured Mudéjar ceiling. Near to the church is a stretch of the Jewish quarter’s original wall.

It is not clear whether El Greco actually lived in or simply near to this house in the heart of the Jewish quarter, now a museum housing a collection of his works. Canvases on display include View of Toledo , a detailed depiction of the city at the time, and the superb series Christ and the Apostles . Underneath the museum, on the ground floor, is a domestic chapel with a fine Mudéjar ceiling and a collection of art by painters of the Toledan School, such as Luis Tristán, a student of El Greco.

This is one of Toledo’s most beautiful Mudéjar monuments. It can be easily identified by its tower, which dates from the 12th-century Reconquest. The church, which was built slightly later, has a beautiful woodwork ceiling. The ornate Mudéjar pulpit and Plateresque altarpiece stand out against the otherwise plain Mudéjar interior.

When Alfonso VI conquered Toledo in 1085, he entered it through this gateway, alongside El Cid. It is the only gateway in the city to have kept its original 10th-century military architecture. The huge towers are topped by a 12th-century Arab gatehouse.