The Spanish Armada

War broke out between Spain and England in 1585. Drake sailed to the New World and sacked the ports of Santo Domingo and Cartagena. On the return leg of the voyage, he captured the Spanish fort of San Agustín in Florida. These exploits encouraged King Philip II of Spain to order the planning for an invasion of England.

In a pre-emptive strike, Drake "singed the King of Spain's beard" by sailing a fleet into Cadiz, one of Spain's main ports, and occupying the town for three days, capturing six ships and destroying 31 others as well as a large quantity of stores. The attack delayed the Spanish invasion by a year.

Drake was vice admiral in command of the English fleet (under Lord Howard of Effingham) when it overcame the Spanish Armada that was attempting to invade England in 1588. As the English fleet pursued the Armada up the English Channel, Drake captured the Spanish galleon Rosario, along with Admiral Pedro de Valdés and all his crew, but causing confusion in the English fleet in the process. The Spanish ship was known to be carrying substantial funds to pay the Spanish Army in the Low Countries. Drake's responsibilities included carrying a stern lantern intended as a guiding light at night for other English vessels opposing the Armada. This exemplified Drake's ability, as a privateer, to suspend strategic purpose if a tactical profit were on offer.

On the night of 29 July, along with Howard, Drake organised fire-ships, causing the majority of the Spanish captains to break formation and sail out of Calais into the open sea. The next day, Drake was present at the Battle of Gravelines.

The most famous (but probably apocryphal) anecdote about Drake relates that, prior to the battle, he was playing a game of bowls on Plymouth Hoe. On being warned of the approach of the Spanish fleet, Drake is said to have remarked that there was plenty of time to finish the game and still beat the Spaniards. This battle was the high point of the remarkable mariner's career.

In 1589, the year after defeating the Armada, Drake was sent to support the rebels in Portugal, which opposed the personal union of Spain and Portugal under King Philip II of Spain in 1580. En route, he sacked the city of La Coruña in Spain. This massive combined naval and land expedition (see "English Armada") was a dismal failure, attributed to a grievous lack of organization, poor training, and paltry supplies. It was a crucial turning point in the Anglo-Spanish War (1585).