Richard Grenville in the context of "Humphrey Gilbert"

Sir Walter Raleigh (/ˈrɔːli, ˈrɑːli, ˈræli/; c. 1553 – 29 October 1618) was an English statesman, soldier, writer and explorer. One of the most notable figures of the Elizabethan era, he played a leading part in English colonisation of North America, suppressed rebellion in Ireland, helped defend England against the Spanish Armada and held political positions under Elizabeth I.

Raleigh was born to a landed gentry family of Protestant faith in Devon, the son of Walter Raleigh and Catherine Champernowne. He was the younger half-brother of Sir Humphrey Gilbert and a cousin of Sir Richard Grenville. Little is known of his early life, though in his late teens he spent some time in France taking part in the religious civil wars. In his 20s he took part in the suppression of rebellion in the colonisation of Ireland; he also participated in the siege of Smerwick. Later, he became a landlord of property in Ireland and mayor of Youghal in east Munster, where his house still stands in Myrtle Grove. He rose rapidly in the favour of Queen Elizabeth I and was knighted in 1585. He was granted a royal patent to explore Virginia, paving the way for future English settlements. In 1591, he secretly married Elizabeth Throckmorton, one of the Queen's ladies-in-waiting, without the Queen's permission, for which he and his wife were sent to the Tower of London. After his release, they retired to his estate at Sherborne, Dorset.

Boscastle (Cornish: Kastelboterel) is a village and fishing port on the north coast of Cornwall, England, in the civil parish of Forrabury and Minster (where the 2011 Census population was included) . It is 14 miles (23 km) south of Bude and 5 miles (8 km) northeast of Tintagel. The harbour is a natural inlet protected by two stone harbour walls built in 1584 by Sir Richard Grenville and is the only significant harbour for 20 miles (32 km) along the coast. The village extends up the valleys of the River Valency and River Jordan. Heavy rainfall on 16 August 2004 caused extensive damage to the village.

Boscastle lies within the Cornwall National Landscape (formerly Cornwall Area of Outstanding Natural Beauty, or AONB). The South West Coast Path passes through the village.

The Battle of Flores was a naval engagement during the Brittany Campaign of the Anglo-Spanish War of 1585 fought off the Island of Flores between an English fleet of 22 ships under Lord Thomas Howard and a Spanish fleet of 55 ships under Alonso de Bazán. Sent to the Azores to capture the annual Spanish treasure convoy, when a stronger Spanish fleet appeared off Flores, Howard ordered his ships to flee to the north, saving all of them except the galleon Revenge commanded by Admiral Sir Richard Grenville.

After transferring his ill crewmen onshore back to his ship, he led the Revenge in a rearguard action against 55 Spanish ships, allowing the English fleet to retire to safety. The crew of the Revenge sank and damaged several Spanish ships during a day-and-night running battle. The Revenge was boarded many times by different Spanish ships, and repelled each attack successfully. When Admiral Sir Richard Grenville was badly wounded, his surviving crew surrendered. Alfred, Lord Tennyson, wrote a poem about the battle, entitled The Revenge: a Ballad of the Fleet.

John White (c. 1539–c. 1593) was an English colonial governor, explorer, artist, and cartographer. White was among those who sailed with Richard Grenville in the first attempt to colonize Roanoke Island in 1585, acting as artist and mapmaker to the expedition. He would most famously briefly serve as the governor of the second attempt to found Roanoke Colony on the same island in 1587 and discover the colonists had mysteriously vanished.

During his time at Roanoke Island, he made several watercolor sketches of the surrounding landscape and the native Algonkin peoples. These works are significant as they are the most informative illustrations of a Native American society of the Eastern seaboard; all of the surviving original watercolors are now preserved in the print room of the British Museum.

The West Country Men were a group of influential individuals in Elizabethan England who advocated the English colonisation of Munster, attacks on the Spanish Empire, and the expansion of the English Empire. The group included Sir Humphrey Gilbert, Sir Walter Raleigh, Sir Francis Drake, Sir John Hawkins, Sir Richard Grenville, and Sir Ralph Lane. Five of these individuals originated in the southwest region of England known as the West Country, and were particularly associated with the seaports of Devon, especially Plymouth.