Settling Point, Anegada by Ricky Dos Santos

The Exploits of
Sir Francis Drake
This famed explorer, who left his imprint on
the Virgin Islands, launched a golden era for England

Story by Claudia Colli

In the dead of the night, a small flotilla of sleek wooden frigates set out from Virgin Gorda heading due west. The destination was Puerto Rico and its rich port of San Juan. At the head of the fleet was England's most daring and celebrated seaman, Sir Francis Drake.

Sir Francis Drake
Sir Francis Drake

The year was 1595 and three decades of fame was behind the portly man with the pointed goatee as he embarked on yet another swipe at Spain's wealthy Caribbean empire. It was to be Drake's last voyage and even though success and more riches would elude him, he would leave his stamp on the area in another way. The route he took as he sailed from Virgin Gorda that November day was a protected, never used channel, dissecting the Virgin Islands from the western tip of Virgin Gorda to the eastern tip of St Thomas – now known as the Sir Francis Drake Channel

Modern day Virgin Islanders have cashed in on Drake's legendary fame. His name has been scattered throughout the Virgin Islands – adding a touch of buccaneer day romance to dozens of inns, pubs and other establishments.

All this is mainly for the benefit of visitors, but if Sir Francis Drake were alive today, he probably would revel in the attention. A cunning and adventurous man, Drake climbed to fame and knighthood through carrying out the kind of daring exploits that other men only dreamt about.

Drake was born in Tavistock, England around 1543 (the actual date is unknown). It was an age of uncertainty for England – the small seafaring nation had just torn itself away from the Pope in favor of Protestantism. It was also a time when Catholic Spain, through its empire in the New World, was the richest country in Europe and the most feared on the sea.

Drake's family were devoutly Protestant and early in childhood they were forced to flee their home because of a Catholic uprising and take refuge aboard an old ship on the Kent coast. Here his father took up preaching at a dockyard and it was at this time that his impressionable son learned to further his love of the sea and distrust of Catholics. He first went to sea on a small vessel running along Britain's coast, all the while waiting for his first opportunity to become an oceangoing sailor. His chance came in 1566 when he was hired on a slave trading ship between Africa and South America, an expedition put together by the famous adventurer, John Hawkins, who was a distant cousin of Drake's.

Taking off from Biras Creek. Photo by Daniel Mejía

Painting of Golden Hind by Paul Garnett, Paul Garnett Studio,

Through early expeditions with Hawkins, Drake came to know the West Indies and the Spanish Main (the richest part of Spain's empire running between South America's Orinoco River and the Isthmus of Panama) learning her points of strength and the location of her treasures.

Even more importantly, he learned that the Spanish Empire was not invulnerable, and it became his mission – almost a holy crusade – to chink away at Spain's armor. Of course, while he was emptying the pockets of Spain's King Phillip, he was also filling his own. None of this escaped the notice of England's Queen Elizabeth, who unofficially underwrote Drake's expeditions enjoying both the political and financial benefits of his ventures.

Over the next decade, he led several expeditions into the New World, all successful politically and financially. Said one observer, "It was such a cooling to King Phillip as never happened to him since he was King of Spain."

In 1577, Drake was summoned to a confidential meeting with Queen Elizabeth, who was the head of a poor, but slowly prospering nation. As one of her favorite officers, Drake was entrusted to fight a highly secret war with Spain in which he was to carry out raids along the western coast of South America, and then search for the exit of the Northwest Passage.

A 16th century Caribbean Map

A 16th century Caribbean Map

The expedition set off later that year with Drake in command of the Pelican (later renamed the Golden Hind) and accompanied by four smaller ships. Along the way, he lost through battles, bad weather and mutiny, his four companion ships. Still, Drake captured several heavily laden treasure ships, transferring their riches to his own vessel. Drake sailed northward along the coast of California, where he set in for repairs. Then, instead of looking for the Northwest Passage, he set sail for England. In 1580, after a total of three years at sea, the Golden Hind returned home, not only filled to the gunwales with treasure, but as the first English ship to circumnavigate the world. Drake came back with riches equaling England's entire yearly revenue, and in return was knighted by a jubilant Queen Elizabeth. The trip dealt another heavy psychological blow to Spain, it wasn't to be Drake's last.

At this time Drake and Hawkins reunited in order to combine their talents as naval strategists. Hawkins was in charge of the Navy's administration, commissioning slim seaworthy ships with heavy guns and small crews that could out sail and outmaneuver Spain's own ponderous vessels. Drake became the admiral to lead Hawkins' ships.

"Drake was entrusted to fight a highly secret war with Spain in which he was to carry out raids along the western coast of South America"

In 1585, Drake had his first opportunity to lead his new navy in battle, for at last, Spain and England were officially at war. During the course of the mission, Drake sacked Santo Domingo and Saint Augustine, Florida and held for ransom Cartagena on the South American coast. It was a costly expedition that in the end made very little money for its investors, but as an operation of war, inflicted a great deal of damage on the enemy.

Even so, King Phillip was far from defeated, and while Drake was forced to sit at home while Queen Elizabeth negotiated peace, Spain was rebuilding its fleet for an attack on England itself. In 1587 Drake set out once again, this time to destroy the Spanish armada in its home port of Cadiz. "Singeing the King's beard" was how the successful operation was later described. But it was too late to stop the armada entirely, and by July 1588 the Spanish fleet closed in on England. In a fierce fight off England's coast led by Lord Admiral Howard and Drake as vice admiral, the armada was destroyed.

It was yet another rousing success for England's greatest seaman. But it was to be his last. By the age of 45 Drake had already seen his best campaigns and from then on was only to experience failure.

A view of the Sir Francis Drake Channel. Photo by Daniel Mejía

A view of the Sir Francis Drake Channel. Photo by Daniel Mejía

In 1589, Drake led an expedition to return the deposed King of Portugal back to the throne in order to further weaken the Spanish empire. The entire operation was badly conceived from the start. Drake no longer exercised the command over his troops that he once had, and discipline was lax. Poor provisioning and inexperienced troops added to the expedition's troubles, but ultimately it was the fact that Drake had lost much of his former daring and nerve, which doomed the mission. When the crucial time came for him to move in and attack Lisbon, he hesitated and lost the advantage.

For the next five years, Drake went into retirement. He lived near Plymouth with his second wife and busied himself with civil matters, sat in Parliament for a while and did some minor work for the Queen. It was a frustrating period for the naval hero, especially as he watched Spain regain her lost momentum.

Finally in 1594 Queen Elizabeth decided to take decisive action against Spain by once again trying to cut off the source of her wealth in the West Indies by attacking the Spanish fleet off San Juan in Puerto Rico. Drake and Hawkins were appointed to lead the new expedition. It was an operation designed to give two aging Elizabethan heroes a second chance, yet the venture seemed ill-fated from the outset. The two men who had worked so closely together in the past disagreed on most vital strategic points concerning the mission. Then, at Guadaloupe, the Spaniards discovered from a captured English vessel that Drake and Hawkins were headed for San Juan and sent five treasure frigates to warn the Puerto Rican city.

Drake and Hawkins knowing that they had lost the vital element of surprise, put in at Virgin Gorda to marshal and redistribute their soldiers – and to perhaps lull the Spaniards into believing they had changed their minds and were going to leave the port untouched. They left Virgin Gorda late at night on November the fourth taking the unpatrolled route now known as the Sir Francis Drake Channel, and arrived at the entrance of San Juan at daybreak. It was too late. The Spanish frigates had beaten the English fleet by two weeks and the harbor was blockaded and impenetrable.

A tough battle ensued, but Drake knew the odds were against him, so he turned the expedition around and headed south towards Panama. He was without Hawkins. The elderly seaman had fallen ill just before reaching the Virgin Islands and had died as they reached the gates of San Juan.

Drake's attack on Panama met with no more success, and for Drake, it signaled the end of his flamboyant career. He now knew he would never be given the command of another fleet. Within a month while sailing off the coast of Honduras, Sir Francis Drake fell ill and died.

It might have been an ignominious end for Drake but it signaled the beginning of a golden era for England. With the help of Drake's earlier exploits, England grew into one of the most feared powers on the sea – singeing the King of Spain's beard once and for all, and building her own rich empire.