Today its maze of narrow, steep and winding streets are packed with monuments of historical and cultural significance that richly reward the visitor for the challenging terrain.

An amphitheatre and an aqueduct are the traces of the Roman past when Titus Livius mentioned Toledo as a "small fortified settlement". The Visigoths that made the city their capital in the 6th Century left behind the San Servando fortress. When the Moors arrived in 711, Toledo was sacked. Its well-to-do and cultured Christian population (Mozarab) was rebellious, and the Muslim rulers had to take drastic measures to subdue it, such as the massacre of the 'Day of the Pit' when some 5000 Toledans were killed. In the 10th Century, the town was given some independence, and a period of peace and prosperity ensued during which scientists and men of letters settled in Toledo. Two mosques have been preserved, as well as segments of the Moorish fortifications (of them, the Vieja Puerta town gate is the most impressive).

In 1085, after the Christian reconquest, King Alfons VI made Toledo his capital. It flourished in an atmosphere of cultural tolerance, Arabs, Jews and Christians living peacefully together. In the 13th Century, the Toledo school of translators translated important scientific and philosophical works from Arabic and Hebrew to Latin, making vast knowledge available to the Europeans for the first time. This came to an abrupt end in the late 15th century with the fall of Granada, when Muslims and Jews were forced to either leave or convert to Catholicism. The town went into decline as Felipe II moved the capital to Madrid. It is today a cultural monument on the UNESCO list of World Cultural Heritage, attracting thousands of tourists.

Of the many remarkable buildings in the city we should first mention the Alcazar (castle). It was first built by the Romans, used by the Moors, rebuilt by Alfons VI, demolished during the Spanish Civil War when General Moscard put up courageous resistance against the Republicans, and subsequently restored to house the Military Museum and the Museum of Knives and Swords.