Sir Walter Raleigh was another of Elizabeth's revered sea dogs, one with whom she would have a tumultuous relationship. Besides being a soldier and a sailor, Raleigh was a poet who at one time had studied law. Driving his seafaring and piratical ambition was the desire to discover and colonize new lands. In 1584, he attempted a voyage to North America, and although the voyage failed, he did conduct some pirate activity while he was attempting the trip. In 1585, he organized a trip to take some 300 colonists to Roanoke Island off the coast of Virginia, but Elizabeth would not allow him to go on the voyage, so Sir Richard Grenville led the journey in his place. The first Roanoke colonists returned to England when they ran out of provisions, but Raleigh later set up a second colony that modern-day scholars and historians continue to debate because the colonists all mysteriously vanished without a trace in 1588.

Queen Elizabeth knighted Raleigh for his service in Ireland, but he consistently fell in and out of the queen's favor. At one point, he even married one of Elizabeth's maids without Elizabeth's permission and was sent to prison in the Tower of London for a time. During another expedition he attempted a trip to South America to find the fabled city of El Dorado, but returned empty-handed. In an effort to regain favor with the queen, he eventually returned to privateering.

After Elizabeth's death in 1603, James I outlawed privateering, and took away several of Raleigh's offices. Raleigh was then convicted of treason in a conspiracy plot against the new king, and subsequently spent thirteen years in prison. After he was released, he led a gold-hunting expedition to Guyana, but en route to their destination Raleigh's partner on the trip led an attack on a Spanish settlement. At the time, King James was attempting to negotiate peace with Spain, and when Raleigh returned from the failed trip, he was beheaded for his part in the attack.