Once the stronghold of Roman, Visigoth, Moor and Spaniard alike, and the historic stomping ground of Charles V of the Holy Roman Empire, El Greco, and Don Quixote, it’s hardly surprising that the central city of Toledo bears that much-coveted UNESCO title. Rising from the banks of the Rio Tagus some forty miles south of Madrid, the old town here is a winding maze of tight-knit cobbled lanes that throws up a spectacular array of architectural gems—from the lichen-studded remnants of the old medieval walls, gates and bridges, to the grand edifice of Toledo Cathedral, complete with its concomitant wealth of artistic masterpieces by Goya, El Greco, Raphael, and Rubens. Then there’s the converted Mezquita Cristo, and the Sinagoga de Santa Maria—one of the last remaining historic synagogues in all of Spain. And once the history has been put to bed, Toledo tour guides often recommend a night time jaunt through the al fresco sangria bars that spill out onto the old streets here, or a shopping trip with a difference in the wealth of antique sword shops adorning the centre.