He was from his earlier days familiar with ships and the sea, and in 1582 he accompanied his uncle, William Hawkins, to the West Indies. In 1585 he was captain of a galliot in Drake's expedition to the Spanish main, in 1588 he commanded a queen's ship against the Armada, and in 1590 he served with his father's expedition at the coast of Portugal.
In 1593 he purchased the discovery ship Dainty, a vessel originally built for his father and used by him in his expeditions, and sailed for the West Indies, the Spanish Main and the South Seas. It seems clear that his project was to prey on the oversea possessions of Spanish crown. Hawkins, however, in an account of the voyage written thirty years afterwards, maintained, and by that time perhaps had really persuaded himself, that his expedition was undertaken purely for the purpose of geographical discovery. After visiting the coast of Brazil, the Dainty passed through the Straits of Magellan, and in due course reached Valparaíso.
Having plundered the town, Hawkins pushed north, and in June 1594, a year after leaving Plymouth, he arrived in the Bay of San Mateo, at the mouth of the Esmeraldas river, nowadays Ecuador, at the position . Here the Dainty was attacked by two Spanish ships. Hawkins was hopelessly outmatched, but Dainty's crew defended her with gallantry. At last, when he himself had been severely wounded, 27 of his men killed, and the Dainty was nearly sinking, he surrendered on 1 July 1594 on the promise of a safe-conduct out of the country for himself and his crew.
Through no fault of the Spanish commander, this promise was not kept. In 1597 Hawkins was sent to Spain, and imprisoned first at Seville and subsequently at Madrid. He was released in 1602, and, returning to England, was knighted in 1603 and elected Mayor of Plymouth the same year. 
In 1604 he became Member of Parliament for Plymouth and Vice-Admiral of Devon, a post which, as the coast was swarming with pirates, was no sinecure. In 1605 he was named in the founding charter of the Spanish Company as one of the 557 founding members. In 1620 to 1621 he was vice-admiral, under Sir Robert Mansell of the fleet sent into the Mediterranean to reduce the Algerian corsairs. He died in London on 17 April 1622.
Hawkins wrote the memories of his trip under the title Voiage into the South Sea (1622), which became the most famous Elizabethan adventure, re-published by the Hakluyt Society in 1847, and reworked in Charles Kingsley's Westward Ho! (1855). He depicts the Spaniards in the Americas in a positive way, judging them as "temperate" and "gentle".
- Chisholm 1911, p. 99.
- Marley 2008, p. 130.
- "List of Mayors and Lord Mayors from 1439 to date". Plymouth City Council. Retrieved 15 June 2014.
- Croft, Pauline, The Spanish Company, London Record Society, Volume 9, London, 1973, see text of 1605 Charter
- Hawkins 1847.
- Hawkins, Sir Richard (1847), Bethune,, Charles Ramsay Drinkwater, ed., The observations of Sir Richard Hawkins, Knt in his voyage into the South sea in the year 1593 :reprinted from the edition of 1622, Hakluyt Society
- Marley, David (2008), Wars of the Americas: A Chronology of Armed Conflict in the Western Hemisphere, ABC-Clio, p. 130, ISBN 1598841009
- This article incorporates text from a publication now in the public domain: Chisholm, Hugh, ed. (1911). "Hawkins, Sir Richard". Encyclopædia Britannica 12 (11th ed.). Cambridge University Press. p. 99.
- Ricardo Hauqhines, "Carta de Ricardo Hauqhines (Hawkins). 6 de agosto de 1594." (in Spanish). Archived from the original on 2012-12-09.