Sir Francis Drake's voyage 1585-1586. 16th century map showing the journey Sir Francis Drake made to the New World from 1585-1586. In 1585 war broke out between Spain and England prompting Drake to sail to the New World and sack the ports of Santo Domingo and Cartagena. On the return leg of the voyage, he captured the Spanish fort of San Augustin in Spanish Florida. These acts of piracy encouraged Philip II of Spain to order the planning of an invasion of England, which became known as The Spanish Armada. This map was created by the Italian cartographer Giovanni Battista Boazio in 1589.