Long the spiritual capital of Spain, Toledo perches atop a rocky mount with steep ocher hills rising on either side, bound on three sides by the Río Tajo (Tagus River). When the Romans came in 192 BC, they fortified the highest point of the rock, where you now see the Alcázar. This stronghold was later remodeled by the Visigoths. In the 8th century, the Moors arrived.
The Moors strengthened Toledo's reputation as a center of religion and learning. Unusual tolerance was extended to those who practiced Christianity (the Mozarabs), as well as to the town's exceptionally large Jewish population. Today, the Moorish legacy is evident in Toledo's strong crafts tradition, the mazelike arrangement of the streets, and the predominance of brick rather than stone. For the Moors, beauty was a quality to be savored within rather than displayed on the surface, and it's significant that even Toledo's cathedral—one of the most richly endowed in Spain—is hard to see from the outside, largely obscured by the warren of houses around it.
Alfonso VI, aided by El Cid ("Lord Conqueror"), captured the city in 1085 and styled himself emperor of Toledo. Under the Christians, the town's strong intellectual life was maintained, and Toledo became famous for its school of translators, who spread to the West knowledge of Arab medicine, law, culture, and philosophy. Religious tolerance continued, and during the rule of Peter the Cruel (so named because he allegedly had members of his own family murdered to advance himself), a Jewish banker, Samuel Levi, became the royal treasurer and one of the wealthiest men in town. By the early 1600s, however, hostility toward Jews and Arabs had grown as Toledo developed into a bastion of the Catholic Church.
As Florence had the Medici and Rome the papacy, so Toledo had its long line of cardinals, most notably Mendoza, Tavera, and Cisneros. Under these patrons of the arts, Renaissance Toledo emerged as a center of humanism. Economically and politically, however, Toledo began to decline in the 16th century. The expulsion of the Jews from Spain in 1492, as part of the Spanish Inquisition, had serious economic consequences for Toledo. When Madrid became the permanent center of the Spanish court in 1561, Toledo's political importance eroded, and the expulsion from Spain of the converted Arabs (Moriscos) in 1601 led to the departure of most of Toledo's artisan community. The years the painter El Greco spent in Toledo—from 1572 to his death in 1614—were those of the town's decline. Its transformation into a major tourist center began in the late 19th century, when the works of El Greco came to be widely appreciated after years of neglect. Today, Toledo is conservative, prosperous, and expensive.
Toledo's winding streets and steep hills can be exasperating, especially when you're looking for a specific sight. Take the entire day to absorb the town's medieval trappings, and expect to get a little lost.
The best way to get to Toledo from Madrid is the high-speed AVE train. The AVE leaves from Madrid eight times daily from Atocha station and gets you there in 30 minutes (the normal train takes 1½ hours). Buses leave every half hour from Méndez Alvaro/Estación del Sur and take 1¼ hours.