Algeciras

After Alfonso XI of Castile beat the Marinids at the Río Salado in 1340, he set out to take the port through which their armies crossed. The siege began in August 1342, with Aragonese, Genoese and Portuguese ships closing the sea, and the defenders of the two walled towns answered with crossbows and early gunpowder bombards. It dragged on for 21 months, through floods, disease and the rout of a Granadan relief army, before Algeciras surrendered on 26 March 1344. Castile never managed to settle it properly, and in 1369 Muhammad V of Granada took it back; ten years later, sure he could not hold it, he had it razed and its people sent away. For more than three centuries the ruins stood empty, until Spaniards fleeing Gibraltar after its capture by an Anglo-Dutch fleet settled among them in 1704, and Algeciras slowly grew into a town again.