Sir Francis Drake’s attack on San Juan was one of the greatest attempted conquests by England in the New World. Although his intention when he left the port of Plymouth was to capture Panama, he diverted to Puerto Rico on hearing that there was a great Spanish treasure. According to rumors, this treasure amounted to two million pesos in gold and silver, and had been brought in by a damaged Spanish ship which was put into San Juan Bay for repairs. Its cargo had been placed temporarily into La Fortaleza, but the repairs had been delayed and the ship had to await the arrival of an escort before returning to Spain.

However, after capturing an English ship, the Spaniards had learned of the plans of Sir Francis and his 1,500 men, and had advised the authorities in San Juan. In the meantime, five frigates under the command of Captain Pedro Tello de Guzmán had arrived from Spain to collect the treasure which lay in La Fortaleza. In all, Puerto Rico’s forces numbered 1,500, including almost 400 men of the regular garrison, 300 from the frigates and around 800 militia. The citadel of San Juan contained 70 artillery pieces of which the majority, including 27 brass cannon, were located in El Morro to protect the harbor entrance and San Juan Bay.

On November 22, 1595, Sir Francis Drake and his 23 ships appeared offshore from San Juan. Drake ordered the burning of the Spanish ships which lay near the entrance of the bay. The flames from one of the burning ships alerted the defenders in El Morro, who opened fire on the English fleet, sinking ten of them. Finally, on the night of November 25, after several attempts, Drake decided to withdraw and proceed to Aguada. There, he repaired his remaining ships, restocked them with food and water, and sailed off to the west, finally leaving Puerto Rican waters on December 3, 1595.

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San Juan National Historic Site, Fort San Cristobal, Norzagaray Street, San Juan, PR 00901
Telephone: (787) 729-6777
Last Update: March, 2000