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Few Spanish cities carry their history as visibly as Toledo. Perched on a granite outcrop above a loop of the River Tagus, the city was once the imperial capital of Castile and the seat of the Spanish Catholic Church, and its skyline, dominated by the Gothic cathedral and the Alcázar fortress, has changed remarkably little since El Greco painted it in the sixteenth century. That continuity is not accidental. Toledo's old city is a UNESCO World Heritage Site, and the dense medieval street plan, with its narrow lanes threading between Mudéjar towers and synagogues, has been preserved with unusual rigour. Walking in from the Puerta de Bisagra, the main gate in the city walls, you enter a place that still feels genuinely inhabited rather than merely curated for visitors.

The old city rewards slow exploration on foot, though the terrain is uneven and the summer heat can be fierce. The cathedral, one of the finest examples of Spanish Gothic architecture in existence, anchors the centre, while the Barrio Judío to the south-west preserves two medieval synagogues, El Tránsito and Santa María la Blanca, that speak to the centuries when Toledo was home to one of the most significant Jewish communities in Iberia. The Monastery of San Juan de los Reyes, commissioned by Ferdinand and Isabella, sits nearby, its cloisters hung with the chains of Christian prisoners freed from Granada. Each of these monuments is within comfortable walking distance of the others, which makes the Toledo Tourist Bracelet a sensible way to approach the cluster, giving access to several of the principal sites under a single arrangement.