If you are a history buff or a fan of pirate stories, you might be interested to learn that the famous English privateer, Francis Drake, who circumnavigated the world, defeated the Spanish Armada was even knighted by Queen Elizabeth I, once tried to raid the island of Puerto Rico in the late 16th century. He finally met his match in the fortified city of San Juan, where he faced fierce resistance from Spanish defenders.

In 1595, Drake led an attack on San Juan’s El Morro Castle with the primary objective of capturing a large treasure of about five tons of gold and silver from a Spanish ship, the Begoña, which had suffered damage at sea and was now in the harbor for repairs.

Puerto Rico’s defenders had prepared for Drake’s arrival by mounting twenty-seven bronze cannons in El Morro. Surveying the city’s defenses, Drake concluded that trying to force his way into the bay with his larger ships would be too risky and instead planned a daring night attack with smaller canoes.

Under the cover of darkness, Drake had some initial success, catching the fort’s soldiers off guard.  However, the English lit fire to one of the Spanish ships defending the mouth of the bay and the light from the burning hull allowed El Morro’s artillerymen to better aim at the attackers, turning the tide of battle. The result was a resounding victory for the defenders, with eight to ten English craft sunk and somewhere between 200 and 400 of Drake’s men lost.

This fascinating piece of history is just one of many you can learn about on our Free Audio Guides tour of El Morro Castle in Old San Juan. All our self-guided audio tours are available on puertorico.freeaudioguides.com and on your favorite podcast player. They are always free and require no equipment rental or app download.