You step onto the van at dawn in Madrid and the city’s hum falls away as the road cuts through Castile’s open plains. In Segovia the Roman aqueduct rises like a stone eyebrow above narrow streets; the Alcázar perches where river valleys meet and the air smells faintly of roasted chestnuts and baking stone. Later, Ávila’s crenellated walls loom—thick, walkable ramparts that still record medieval lines of defense. By late afternoon Toledo’s hilltop profile tightens: a jumble of churches, synagogues and mosques folded into alleys that slope toward the Tagus.