John Hawkins followed early in his father’s footsteps. His earliest voyages were made when quite a young man to the Canary Islands. How he came to engage in the slave trade between the African coast and the West Indies Hakluyt thus naïvely relates:
“Master John Haukins having made divers voyages to the Iles of the Canaries, and there by his good and upright dealing being growen in love and favour with the people, informed himselfe amongst them by diligent inquisition, of the state of the West India, whereof he had received some knowledge by the instructions of his father, but increased the same by the advertisements and reports of that people. And being amongst other particulars assured that Negroes were very good merchandise in Hispaniola, and that store of Negroes might easily be had upon the coast of Guinea, resolved with himselfe to make triall thereof, and communicated that devise with his worshipfull friendes of London; namely with Sir Lionel Ducket, Sir Thomas Lodge, M. Gunson, his father in law [Benjamin Gonson, then treasurer of the navy], Sir Wm. Winter [also of the navy], M. Bromfield and others. All which persons liked so well of his intention, that they became liberall contributers and adventurers in the action.”
The first voyage of this enterprise was made in 1562–1563 with a fleet of three ships and a company of one hundred men. Sailing in October he touched first in his course at Teneriffe. Thence he passed down to the Sierra Leone Coast, where he stayed “some good time” and collected, “partly by the sword and partly by other meanes,” at least three hundred Negroes, whom he packed in his ships, besides “other merchandises which that countrey yieldeth.” With this “praye” (prey) he sailed over the “ocean sea” bound for Hispaniola—San Domingo. Arriving at the port of Isabella he there disposed of some of the English commodities he had brought out, and a part of his living freight, meanwhile alert, “trusting the Spaniards no further then [than] by his owne strength he was able still to master them.” Thence he went to Porto Plata, where he made his sales, while, as at Isabella, “standing alwaies [always] on his guard”; and lastly to Monte Christi, disposing there of the remainder of the Negroes. In these three ports he took by way of exchange “such quantitie of merchandise that he did not onely lade his owne 3 shippes with hides, ginger, sugars, and some quantitie of pearles, but he freighted also two other hulkes with hides and other like commodities which he sent into Spaine.” Then he returned to England with “much gain to himselfe and the aforesayd venturers” as the outcome of this voyage. The two hulks sent to Spain were seized at Seville as smugglers, under the law of the country against unlicensed trading in the Spanish colonies, and their goods confiscated. These Hawkins valued at twenty thousand pounds. Notwithstanding their loss the balance of the profits remained large.