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Santa María la Blanca — start here, because it's the whole idea in one room. Built around 1180 as a synagogue, by Muslim architects, under a Christian king. Thirty-two horseshoe arches, whitewashed octagonal pillars, pine-cone capitals that only show when raking afternoon light hits them. ~€4. Go on a bright day.
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Sinagoga del Tránsito & Sephardic Museum — the grander of the two surviving synagogues, its walls carved with Hebrew and Arabic in the same Mudéjar plaster, paid for by Samuel Ha-Levi, a Jewish treasurer to Pedro I of Castile. €3, free Saturdays from 2PM and Sundays. The museum runs to the 1492 expulsion; the tombstones in the garden are the quiet part.
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Iglesia de Santo Tomé — the single greatest painting in the city: El Greco's 'The Burial of the Count of Orgaz.' It still hangs above the tomb it depicts. ~€4, and get there for the 10AM opening, before 11 when the groups arrive.
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Mezquita del Cristo de la Luz — the oldest building standing in Toledo, a mosque from the year 999. It's the size of a garage, and the architect gave every one of its nine vaults a different design just to show off. Roman road paving sits under glass at the door. €3.
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Toledo Cathedral — the Christian statement, begun 1226 over the main mosque, and effectively an art gallery with a nave attached. El Greco's 'El Espolio,' a Goya, a Titian and a Caravaggio share the sacristy. ~€12.50.
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Monasterio de San Juan de los Reyes — Ferdinand and Isabella's Isabelline-Gothic power move, hung with the chains of Christian captives freed at Granada in 1492. ~€4.
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Museo del Greco — not actually his house (a marquis rebuilt it in 1911), but the collection is real, including the extraordinary 'View and Plan of Toledo' and the full Apostolado series. €3, free Saturday afternoon and Sunday. The original 14th-century Mudéjar cellar underneath is the coolest room in the city in August.
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Fábrica de Espadas Mariano Zamorano (Calle Ciudad 19) — Toledo armed Europe for 2,000 years, and this family forge, going since 1870, is one of the last places still hammering blades by hand rather than importing them from Albacete. Free to walk in; ask nicely and they'll usually let you watch the tempering.
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A damascene workshop on Paseo de Recaredo — the city's other craft: 24-carat gold wire hammered into blackened steel one thread at a time, then fired and burnished. Watch it at the bench and you'll finally understand why the real pendant costs €60 and the identical-looking souvenir costs €8.
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Museo de Santa Cruz (Miguel de Cervantes 3) — free, and nobody queues. A 16th-century hospital with a Plateresque doorway carved like sugar-work, holding several El Grecos including his 'Assumption' and an enormous 16th-century Zodiac wall-hanging.