Toledo, Spain

Toledo rises on a hill above the Tagus River roughly 70 kilometers south of Madrid, with about 85,000 residents living within its medieval walls. UNESCO listed the city in 1986 as the "City of the Three Cultures," where Christians, Muslims, and Jews shared the streets following the 1085 Reconquista. The 1226 Gothic cathedral holds an 18-panel altarpiece carved by Enrique de Egas in 1495, and the Synagogue of Santa María la Blanca, dated to 1180, ranks as the oldest surviving synagogue in Europe. El Greco settled here in 1577, and his 1586 Burial of the Count of Orgaz still hangs in the Santo Tomé church, where one detail continues to puzzle historians.