The Tagus wraps three sides of the rock, so every way into the town is uphill. Christian, Muslim and Jewish buildings survive inside one wall, and after the capital left for Madrid in 1561 it stopped growing and kept that frame. The train takes just over half an hour, so many come for the day.
01Toledo Cathedral
Fifty-four panels on the lower choir stalls log the conquest of Granada, one fort at a time. The carver went along, so place names and wall shapes match. El Greco hangs in the sacristy. It is a working vestry, not a gallery, so viewing stops during mass.
A square block on the summit, in sight from any lane. A siege of more than two months in 1936 brought half of it down, and it was raised again afterwards. It holds the army museum and a library now, and the basement shows excavated Roman walling.
Hebrew and Arabic run side by side along the upper wall. A Jewish treasurer paid for it, Muslim carpenters roofed it, and today it is the Sephardic museum. Santa Maria la Blanca next door is a synagogue of the same era, bare white columns, opposite in feel.
You go in for a single painting, and that room holds nothing else. El Greco made it for this church and it has never left the spot it was painted for. The mourners along the bottom are taken to be Toledo men of his day.
A small mosque of 999, its brick arches dividing nine bays with a different vault over each. On the slope outside, excavated Roman paving lies uncovered. The room is tight enough that ten people fill it.
Climb it when the sun is low. From the hill across the river to the south the whole town shows as a shape wrapped in water, and the walk up takes about an hour with almost no shade.
Chains hang in rows along the outside wall. They are the irons worn by Christian captives freed at Granada, brought back and fixed there. The cloister garth is planted with orange trees, so it stays green through winter.
The main gate on the north wall carries a large double-headed eagle of Charles V above it. The yard between the outer and inner arches is a trap with no way through. Whoever came in was held there under walls that looked down on them.
An open-air escalator lifts you the forty metres from the car park below the wall into the old town, broken into several flights. It stops at night, so late arrivals take the steps, but by day it saves dragging a bag over the hill.
Built as a synagogue in the late 12th century and later turned into a church. Rows of whitewashed horseshoe arches stand on octagonal pillars whose capitals are carved with pine cones. The wristband pass that covers several city monuments gets you in.
A hospital raised in the 16th century's first years under Cardinal Mendoza's will, its front thick with plateresque carving. Long halls arranged in a cross plan hold several El Grecos and tapestries. Downstairs are Toledo and Talavera ceramics.
A museum in the Jewish quarter set up as a house of El Greco's day. It hangs his View and Plan of Toledo, the city drawn like a map, and his series of the twelve apostles. A 16th-century courtyard house and a garden are part of the visit.
Stone arches of the 14th century carry this crossing over the Tagus on the west, a gate tower at each end. The old town on its cliff, seen from the deck, is the postcard angle. Below it, a riverside path loops around the city.
The baroque Jesuit church on the highest ground of the old town. From its twin front towers the cathedral spire and the Alcazar sit at eye level. The line moves faster than the cathedral's; for the view alone, come here instead.
Twelve white windmills and a castle in a line along a ridge over the La Mancha plain south of Toledo. These are the giants Don Quixote charged at. Some of the mills open inside to show the millstones and sail gear.