The major settlement on northern shore of Puerto Rico.
22/11/1596 - The flagship of the Tierra Firme Treasure Fleet, under Sancho Pardo Osorio, lay in harbour after being dismasted. The town was attacked by Francis Drake. The defenders were supported by 5 frigates sent from Spain, a galleon sunk across the harbour mouth with chains and logs as a barrier, with 1500 soldiers, 800 seamen, and 9000 armed civilians, including a company of lancers under the Governor's command. After severe losses, Drake was beaten off.
15/6/1598 - attacked by Clifford. The town was reduced in defences due to plague, having 134 soldiers, 24 gunners, and 200 recently arrived men. Clifford atatcked with 500. Governor Antonio Mosquera took his forces to the El morro castle and held out until they ran out of food. Clifford returned to England with the church bells, organ, 1000 crates of sugar, 2000 quintales of ginger, and a ships cargo of pearls, and another of slaves. His garrison left behind blew up part of El Morro after the town refused to pay tribute, and followed him home. The Spanish began constructing new fortifications.