Simon Fernando

Benedetto Robinson as Simon Fernando in the 2025 production of The Lost Colony

The Lost Colony, Roanoke Island Historical Association

Quick Facts

Significance:

Portuguese sailor who worked for both the Spanish and English

Place of Birth:

Terceira, the Azores

Date of Birth:

C. 1538

Place of Death:

Unknown

Date of Death:

C. 1590

Place of Burial:

Unknown

The infamous ship pilot on the 1584, 1585, and 1587 English voyages to Roanoke Island, Simon Fernandes (Fernandez or Fernando are also used) played an important role in getting the English to the New World. His allegiances, motives, and even his character are often called into question when trying to determine what role he played in the Lost Colony's disappearance. 

Born Simão Fernandes (Fernandez) in the Azores around 1538, he studied to be a pilot at the Spanish Casa de Contratación in Seville. This training consisted of detailed lecture, study of charts and stars, rigorous testing and finally, the awarding of the title "Pilot." Portuguese by birth, Fernandes served as a pilot for the Spanish until 1570 when he moved to the Bristol Channel in England. He settled in Cardiff and started working for William Herbert as a pirate. Herbert was the brother of an important member of Queen Elizabeth I's Privy Council, which gave him protection. Fernandes quickly began earning money, soon purchasing his own ship and becoming more powerful. He was arrested and put in prison at one point, but typically operated unchecked. In March of 1577, pressure from Portugal over an attacked ship led Queen Elizabeth to imprison Fernandes in London. While in London, (perhaps while still in prison) Fernandes started working for Sir Francis Walsingham, the Queen's Spymaster. 

Having formerly worked for the Spanish, Fernandes was a wealth of information on their routes, cartography, and treasure fleets. By exposing Spanish information, he set himself up for great success in English privateering and exploration. Fernandes converted to the Church of England and married an Englishwoman, quickly putting roots down in his newly adopted country. He began privateering, or pirating with permission from the government to steal from other countries. The Spanish government was enraged by his change of loyalty, but ultimately, there was nothing they could do. Fernandes quickly climbed the ranks of English explorers. 

Fernandes soon became involved in English attempts to colonize North America. With his detailed knowledge and previous trips, he was the ideal pilot for Englishmen attempting to see the New World. In 1578-79, he accompanied Sir Walter Raleigh on a failed attempt to find the fabled Northwest Passage. In 1580, he took Sir Humphrey Gilbert on a reconnaissance of the North American coastline. Fernandes also met with notable cartographers of the time to help contribute to new English maps. In 1582, he led the first English trade mission to Indonesia for spices organized by a rival of Sir Walter Raleigh. The mission ultimately failed, never making it out of the Atlantic Ocean, but the chaplain provided a wealth of information. Richard Madox, the chaplain on the voyage left a scathing commentary on Fernandes's character, calling him "a ravenous thief with talons more rapacious than any vulture." He reported that Fernandes claimed to have protection from five Privy Councilors to wage war on the Spanish. These claims provide evidence he was a member of the growing anti-Spanish movement in England. However, there were still those that believed Fernandes was a double agent working for the Spanish. 

On April 27 1584, Simon Fernandes departed from England piloting one of the two ships under the direction of Philip Amadas and Arthur Barlowe. The expedition, with Raleigh as its patron, was searching for a site to create a privateering base in the New World. Fernandes was an obvious choice for the trip. With his previous experience in the New World, he could help Amadas and Barlowe successfully establish contact with native tribes and find an ideal location for Raleigh's base. In July, they arrived on Roanoke Island and stayed for a few weeks. Barlowe wrote glowing accounts of the New World, and two members of local Algonquian tribes, Manteo and Wanchese, joined the English for the voyage home. Fernandes was immediately recruited for Raleigh's second planned voyage and began preparing for a return to Roanoke Island. 

On April 9, 1585, Fernandes once again set out for the New World on a voyage backed by Sir Walter Raleigh. This time, he was piloting the Tyger, flagship of Sir Richard Grenville's seven ship fleet. Six hundred men were on the voyage, most of them sailors, to set up a military colony and privateering base on Roanoke Island. Also aboard the Tyger were several notable members of the expedition. They included scientist Thomas Hariot, artist John White, newly-appointed governor Ralph Lane, and the Carolina Algonquian translators Manteo and Wanchese. The fleet was soon separated by a storm, forcing the Tyger to arrive in the Caribbean before the rest of the ships. Grenville took advantage of the opportunity to engage in some privateering, angering Lane who wanted to sail ahead to Roanoke and give the colony time to prepare. The ship Fernandes piloted did not arrive to Roanoke Island until the end of June. Immediately upon arriving in the Outer Banks, Fernandes led the Tyger into the Pamlico Sound, but a storm caused the ship to run aground. 

The damage to the ship was repairable, but the biggest loss were the supplies for the military colony. Grenville and others were quick to blame Fernandes and his skill for the loss of supplies. Lane however, wrote that Fernandes had not been the cause of the devastation. No matter who or what was to blame, the colony no longer had the supplies to support six hundred men. One ship was dispatched back to England to inform Raleigh of their arrival and the need for more supplies, with the other ships staying a little longer to help Lane's military colony set up. The Tyger left Roanoke Island for England on August 25, taking Grenville and Fernandes back across the sea. The voyage took them through a few storms, but they arrived back in England on October 18. 

Simon Fernandes's next voyage was also his most well known. On April 26, 1587 117 colonists departed England in three ships bound for the Chesapeake Bay. This new venture, to be called the "Cittie of Ralegh," was to be governed by the artist, John White. Simon Fernandes was hired as the pilot to escort them to the New World. The voyage was rough, with illness and storms popping up repeatedly. As they sailed the Caribbean, misfortune befell them even further. Contaminated water, dwindling supplies, and rising tension between White and Fernandes forecast trouble on the horizon for the voyage.

When they arrived just off of Roanoke Island, intending to send a search party for the 15 men left in 1586, Fernandes proclaimed (according to White) that everyone must go ashore here, and he would take them no further because it was too late in the summer. Exactly what happened to cause the colonists to be put ashore on Roanoke Island is unknown. It is possible the two pregnant women aboard, Eleanor Dare and Margery Harvie, wanted to go ashore before they gave birth and White blamed Fernandes. Fernandes was also more knowledgeable when it came to ocean travel and may have felt it was unsafe to continue. Fernandes could have also wanted to engage in privateering and needed the colonists gone to do so. The animosity between White and Fernandes could have reached a breaking point and drastic measures were taken. Whatever the reason, the colonists arrived on Roanoke Island, roughly 90 miles from their intended destination, on July 22, 1587. 

Fernandes and the other two ships did not leave the colonists immediately. They stayed to resupply and perform repairs before they ventured back out to sea. When they departed on August 27, John White accompanied them back to England. The return trip too, was full of illness and storms, with several men dying on the voyage. By the time they limped into an Irish port, it was October 16. After this point, not much is known about Fernandes. He helped the English fight the Spanish Armada in the late 1580s. Simon Fernandes's last known voyage was to the Azores in 1590. It is believed he died on that voyage. 

What role Fernandes played (if any) in the disappearance of the Lost Colony is still unknown to this day. His skills as a pilot were a valuable asset to Raleigh's expeditions and attempted colonies in the New World. Fernandes's questionable past as a privateer and Spanish pilot will forever cast doubt on his intentions with the Lost Colony. Unless more information is uncovered, Simon Fernandes will always be a hero to some and a villain to others.