The spiritual capital of Castile, Toledo sits atop a rocky mount surrounded on three sides by the Río Tajo (Tagus River). When the Romans arrived here in 192 BC, they built their fortress (the Alcázar) on the highest point of the rock. Later, the Visigoths remodeled the stronghold.

In the 8th century, the Moors arrived and strengthened Toledo's reputation as a center of religion and learning. Today, the Moorish legacy is evident in Toledo's strong crafts tradition, the mazelike streets, and the predominance of brick construction (rather than the stone of many of Spain's historical cities). For the Moors, beauty was to be savored from within rather than displayed on the surface. 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 dubbed 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 taught Arab medicine, law, culture, and philosophy. Religious tolerance continued, and during the rule of Pedro the Cruel (so named because he allegedly had members of his own family murdered to advance his position), a Jewish banker, Samuel Levi, became the royal treasurer and one of the wealthiest men in the booming city. By the late 1400s, however, hostility toward Jews and Arabs had grown as Toledo developed into a bastion of the Catholic Church.

Under Toledo's long line of cardinals—most notably Mendoza, Tavera, and Cisneros—Renaissance Toledo was a center of the humanities. Economically and politically, however, Toledo began to decline at the end of the 15th century. The expulsion of the Jews from Spain in 1492, as part of the Spanish Inquisition, eroded Toledo's economic and intellectual prowess. When Madrid became the permanent center of the Spanish court in 1561, Toledo lost its political importance, and the expulsion from Spain of the converted Arabs (Moriscos) in 1601 meant the departure of most of the city's artisans. The years the painter El Greco spent in Toledo—from 1572 to his death in 1614—were those of the city's decline, which is greatly reflected in his works. In the late 19th century, after hundreds of years of neglect, the works of El Greco came to be widely appreciated, and Toledo was transformed into a major tourist destination. Today, Toledo is conservative, prosperous, and proud—and a bit provincial (don't expect cosmopolitan luxury here). Its winding streets and steep hills can be exasperating, especially when you're searching for a specific sight, so take a full day (or three) to absorb the town's medieval trappings—and expect to get a little lost.

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