[11] In 1592, he participated in the Cruising Voyage to the Azores Islands, collaborating in the capture of the Portuguese carrack Madre de Deus[12] with a rich cargo, and a 600-ton Biscayan ship loaded with iron.

[13][14][15] In the brief career of the ship it had already demonstrated good attributes, but Hawkins' father considered that it "never brought but cost, trouble and care", so, as a businessman, he decided to sell it to his son.

[17][16] On 12 June 1593, after Hawkins obtained a letter of queen's mark, he sailed from Plymouth[16] to South America with the flagship Dainty and two other ships that formed his squadron; the 100-ton storeship Hawk and the 60-ton pinnace Fancy.

[17] Historians say that the crew of the Dainty and the other ships were of very poor quality, which would explain the delay they had in passing the English Channel and the three months in the Canary Islands.

On November 10, Hawkins approached Santos (Brazil) with his squadron for provision, and five days later he anchored off Santa Ana Island to establish a camp.

[17] In the same month, while sailing near the Río de la Plata, the Dainty lost contact with the Fancy, which after separating reversed its course to England.

[21] The Spaniards sailed the Dainty to the Pearl Islands and then to the port of Perico (west-northwest of Panama City[22]), having a jubilant reception on 9 July.

[27] During Viceroy Luis de Velasco's rule (1596–1604), it remained permanently enlisted since Dutch intruders entered the South Pacific[5] between 1599 and 1600.

[30] In the middle of that year, it stayed in Callao to protect the port, with 30 men and 12 guns, from the threat of the Dutch squadron under Joris van Spilbergen.

[31][E] Shortly after, it set sail for Panama in a convoy, carrying money from the Royal Treasury and private sector, and to bring the new Viceroy of Peru, the Prince of Esquilache.