Sir Walter Raleigh’s Adventurous Life: Sailor, Soldier, Scholar

Sailor, solider, poet; discover the exciting life of adventurer Sir Walter Raleigh.

Jul 18, 2023By Cale Gressman, BA History, BA Philosophy

sir walter raleigh life life


Sir Walter Raleigh was born around 1554 to Walter Raleigh and Catherine Champernowne near the village of East Budleigh in Devon, England. Coming from a family of committed Protestants, Raleigh would develop an enmity towards Roman Catholicism after several near-escapes under the reign of Queen Mary. In one incident, his father was forced to hide in a tower to avoid being executed for his faith. This would lead a young Walter Raleigh to serve in the Huegonot Army in France during the French Wars of Religion in 1569. It was the first of his many adventures.


Sir Walter Raleigh: The Irish Prelude

siege of smerwick
Map of the Smerwick attack, 1580, via Cambridge University Press


In 1580, Raleigh would serve in the Queen’s army in Ireland during the Desmond Uprisings. Here Raleigh would distinguish himself at the siege of Smerwick, as well as by overseeing efforts to settle English and Scottish Protestants in the historical region of Munster. Comprised of the lands seized from the Earl of Desmond, this area would become known as the Munster Plantation. According to historian Ian N. Gregory “The significance of the Munster plantation is that it left a large Protestant minority in south and west Cork.” These actions helped bring Raleigh to the attention of Queen Elizabeth and he became her favorite in court by 1582.


For his actions in Ireland, Mr. Walter Raleigh would become Sir Walter Raleigh in 1585. Moreover, Raleigh would be given a large estate in Ireland and trade privileges, and he would be appointed to Parliament. Most important to his legacy, however, was that he was granted the right to establish a colony in the New World.


Virginia and the Lost Colony

sir walter raleigh croatoan
The Lost Colony, design by William Ludwell Sheppard, engraving by William James Linton, 1876, via Lincoln Financial Foundation Collectio


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In 1587, Raleigh would make good on these granted privileges by exploring along the coast of present-day North Carolina to Florida, which he named Virginia after Queen Elizabeth, the “Virgin Queen”. It would be in this region that Raleigh would attempt to plant England’s first colony in North America.


Located in what is now the Outer Banks of North Carolina, the attempted English settlement at Roanoke was composed of two separate expeditions. The location was chosen for its proximity to Spanish holdings in the Caribbean that the English hoped to unleash their privateers on. The first expedition was sent by Raleigh in 1585. Composed of 108 men, quarreling, disorganization, and hostile natives would force the colonists to return to England in 1586.


two places roanoke island
Aerial view of Roanoke Island, via


A second attempt was made in 1587, with 114 settlers. However, this too would fail. The mayor of the little settlement, John White, would leave the island the same year to return to England to request more supplies and manpower. However, he would be delayed for over three years by the outbreak of the Anglo-Spanish War, which forced him to arm his merchant vessel to engage in the conflict.


By the time he returned in 1590, he would find the settlement abandoned with only the words CROATOAN and CRO carved into the trees within the colony’s borders. John White and his crew were unable to immediately go in search of the missing colonists due to an encroaching storm. The mystery of the Lost Colony of Roanoke persists to this day. However, this attempt by Raleigh to establish a colony in the New World served as a prelude or perhaps as the beginning of the British Empire.


The Armada

fire ships spanish armada
Launch of English fireships against the Spanish Armada, 7 August 1588, c. 1590, Royal Museums Greenwich


While those at Roanoke were left to their unknown fates, Raleigh was busy fighting the Spanish. When the English had heard that the Spanish were preparing a massive armada to invade England, Sir Francis Drake, a distant relative to Raleigh, made a preemptive strike on the port of Cadíz in Spain in 1587. This forestalled the invasion for a year, but the Armada would launch in 1588. Many of England’s most famous Sea Dogs, including Sir Walter Raleigh, would participate in the defense of the island.


By July of 1588, a Spanish Armada, under the command of the Duke of Medina-Sidonia, and made up of approximately 150 ships and 18,000 men, was in the English Channel. To confront them, were around 100 English vessels under the command of Lord Howard of Effingham. After several small engagements, the English quickly realized that they could not break the Spanish Armada’s half-moon formation.


The Spanish would anchor at Calais Roads off the coast of France so that they could rendezvous with a Spanish army led by the Duke of Parma, an Italian noble and condottiere.  This is when Howard and Sir Francis Drake came up with the plan to use fireships to break the formation. On August 8 at midnight, the English would set fire to eight unoccupied ships and send them toward the Spanish fleet. The attack succeeded in scattering the Armada; driving them into the open sea. At dawn, the English would attack the scattered vessels at the Battle of Gravelines, where they succeeded in sinking several Spanish vessels.


defeat of the spanish armada
Defeat of the Spanish Armada, 8 August 1588, by Philippe-Jacques Loutherbourg, 1796, via Royal Museums Greenwich


However, it would ultimately be the weather and disease that ended the Armada’s chances. Heavy winds would push the fleet out into the North Sea, ending any chance of linking up with the Duke of Parma’s army. Disease, too, was setting in. The Spanish belatedly decided to make the long journey home. Of the 130 ships and 18,000 men that would begin the voyage, approximately 60 ships, and 15,000 men would be lost. Raleigh’s impact and role in the battle are somewhat vague. However, it is known that he participated in the defense.


To the Tower and Eldorado

tower of london aerial view
The Tower of London, photo by Duncan, 2013, via Wikimedia Commons


It was during this period that Raleigh secretly courted and married Elizabeth Throckmorton, a lady-in-waiting of Queen Elizabeth, and had a son together who they named Walter. This was discovered in 1592, and a jealous Queen Elizabeth would banish Raleigh, who for so long had been her favorite, from the court. He and his wife would be sent to the Tower of London.


Tragically, the baby would die from the plague while in the Tower, and feeling sorry for the grieving mother, Queen Elizabeth allowed her former lady-in-waiting to leave. Raleigh would also leave the tower several months later, after a privateering expedition he had invested in brought enough profit for him to buy his freedom.


gold raft el dorado
Gold raft treasure, from Pasca Cundinara, via Flickr/Pedro Szekely


To regain the favor he had lost with the Queen, he decided to go looking for a legend. That is the city of El Dorado (or Eldorado), which stories stated was a literal city of gold. In 1595, Raleigh would launch an expedition to South America in search of this legend.


He and his expedition would leave for South America on February 6, 1595, and make their way to present-day Guyana. It had long been rumored that the City of Gold lay somewhere beyond the mouth of the Orinoco River. On their way there, the English would land in Trinidad and capture the Spanish leader Don Antonio de Berrior, who had also searched for the fabled city. Raleigh would force him to reveal what he knew. The Englishmen would arrive at the Orinoco River and make their way up it but to no avail. They would be forced to abandon their search and head home by August 1595.


Though the trip was a technical failure, Raleigh attempted to salvage it by writing The Discovery of the Large, Rich, and Beautiful Empire of Guiana: With a Relation of the Great and Golden City of Manoa… Etc. This was an attempt to encourage the colonization of present-day Guyana. The book described the region that he and his men had explored, including the rivers, topography, flora, and fauna that he had seen along the way. The book was successful but was a poor pittance in comparison to a city of gold.


Twilight Years

storming of cadiz sir walter raleigh
The 1596 Capture of Cádiz, from British Battles on Land and Sea, volume 1, 1876, via British Library


This was not quite the end for Raleigh. In 1596, he, under the command of the Earl of Essex, would launch a somewhat successful raid on the Spanish port of Cadíz, where he would be wounded in the fighting. While the expedition succeeded in sinking two ships and leaving the city in flames, they did not do enough damage to prevent another Great Armada from being built.


The following year, he would serve as a rear admiral in the unsuccessful Islands Voyage against the Azores. While on their return trip, Raleigh and the English fleet would help defend England against the Third Spanish Armada, which as before would ultimately be destroyed in the stormy North Sea.


By this point, Raleigh had gotten back in favor with Queen Elizabeth. He would be chosen as a member of parliament for Dorset (1597) and Cornwall (1601). He would serve as the Governor of Jersey from 1600-1603. However, this period of favoritism would not last. In 1603, Queen Elizabeth would die leaving the throne to King James I.


Back to the Tower

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Tower interior, Tower of London, photo by Kjetil Bjørnsrud, 2005, via Wikimedia Commons


The same year that King James I ascended the English throne, Raleigh would be swept up in accusations of treason. It was alleged that he was part of a wider plot to depose King James I. The evidence of this was flimsy, but he would nonetheless be put on trial. He would be convicted of treason and sentenced to death. To await his execution, he would be sent back to the Tower of London. Soon after, King James I would show mercy and reduced his sentence from death to life imprisonment.


While in the Tower, Raleigh devoted his time to writing A History of the World. He was also known to study chemistry and other sciences and was a poet. Although most of his work was written during the latter part of the 1580s as a way to maintain favor with Queen Elizabeth. Raleigh would spend 13 years in the Tower, although, as evidenced by the fact that he could write so extensive a book, he was not without material comforts, and his family was allowed to come and visit him.


The Attack That Shouldn’t Have Happened

sir walter raleigh young
Sir Walter Raleigh, by the “H” Monogrammist, 1588, via the British Library


In 1616, Raleigh would be released from the Tower, however, he was not pardoned for his crime. Attempting to gain the favor of England’s monarch, he would convince King James I to allow him to launch an expedition to modern-day Venezuela to attempt to establish a gold mining operation there. He swore that he would do this without offending the Spanish, who controlled the area.


King James’ coffers were nearly empty, so he hesitantly agreed so long as Raleigh avoided conflict with the Spanish. Raleigh knew there was little chance of actually discovering gold in the area, but planned to raid Spanish shipping in the area. He hoped that if he and his expedition seized enough booty, he would hopefully be forgiven by England’s king. So that same year he headed to Spanish South America.


Needless to say, the expedition ended in disaster. The English, upon arriving in South America, once again made their way up the Orinoco River, but Raleigh was struck down with a severe fever which prevented him from leading his men further. His Lieutenant Lawrence Kemys, who was a long-term friend and subordinate of Raleigh, was charged with leading the rest of the expedition upriver.


Soon after, Kemys and his men would get into a brief skirmish with the Spanish garrison at the outpost of Santo Tomé, where Raleigh’s son Walter would die. After occupying the settlement for some time, Kemys ordered it looted and burned. Upon his return, Kemys begged Raleigh’s forgiveness for his actions. When Raleigh refused to grant this, Kemys immediately committed suicide.


The Death of Sir Walter Raleigh: Strike Man! Strike!

execution of sir walter raleigh
The execution of Sir Walter Raleigh, from The Popular History of England: An Illustrated History of Society and Government from the Earliest Period to Our Own Times, by Charles Knight, c. 1860, via the History Press


Raleigh and his men would return to England as failures. The Count of Gondomar, the Spanish Ambassador to England, furiously demanded Raleigh’s death for his violation of the peace between Spain and England. King James I, already distrustful of Raleigh, agreed. In 1618, he would be sentenced to death for treason, his original charge from 1603. He would be sent back to the Tower where he had spent so many years.


On October 29, 1618, 64-year-old Sir Walter Raleigh would be brought to the courtyard of the Palace of Westminster. Here he reportedly faced death resolutely. It is claimed that he encouraged a hesitant executioner with the words, “Strike Man! Strike!” Rather gruesomely, Raleigh’s severed head would be given to his widow, who would have it embalmed and kept it in her possession until her death 29 years later.


The legacy of Sir Walter Raleigh is multi-faceted. While the likes of Sir Francis Drake are known primarily for their privateering adventures, Raleigh was a sailor, soldier, and scholar, not to mention a politician and a poet. Raleigh’s legacy has a distinct hint of tragedy to it. A tragedy in that his meteoric rise to prominence was thanks to Queen Elizabeth’s favor, and his meteoric fall was caused by the ascension of King James I. Regardless, Sir Walter Raleigh stands today as one of England’s greatest sailors.

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By Cale GressmanBA History, BA PhilosophyCale was born in Colorado and currently lives in Northern Minnesota. He completed his BA in History, Philosophy, and Religion at the University of North Dakota and graduated in May of 2022. He is taking a gap year before applying for graduate school to complete his PhD in history. He is passionate about history in a wide range of areas, including American, European, military, and intellectual/philosophical history. He also enjoys writing and historical research.