An air of dwindling majesty sweeps through the wind-lashed, whitewashed streets of Medina Sidonia. This strategic hilltop town, 30km north of Vejer de la Frontera, was once the seat of the Duques de Medina Sidonia – one of Spain's most powerful families, descended from Reconquista hero Guzmán El Bueno.
Medina Sidonia's hillock has been inhabited since early prehistoric times, and the Phoenicians, Romans and Moors all established settlements here. The town was reconquered for the Christians in 1267 by Alfonso X El Sabio and, from 1445, flourished under the Ducado de Medina Sidonia. Today, topped by a ruined castle of Roman origin and a Gothic-Renaissance church, and with an excavated Roman calzada (road) open for visits, history-rich Medina is very much worth exploring, yet it remains off southern Andalucía's beaten track. It's an easy day trip from Vejer, Arcos (40km north) or Jerez (35km northwest).