He returned to England in January, 1672, and retired to the house of his brother in Somersetshire, where he remained all the ensuing summer. In 1673, he entered on board the Prince Royal, commanded by the famous Sir Edward Spragge, and was in two engagements that summer against the Dutch. He afterwards returned to his brother’s house, where he met with one Colonel Hellier, who had a large estate in Jamaica, and who persuaded him to go over to that island, where he was some time employed in the management of that gentleman’s plantation. Not liking the life of a planter, which he continued somewhat more than a year, he engaged among the logwood cutters, and embarked from Jamaica for Campeachy, in August 1675, but returned to Jamaica in the end of that year. In February 1676, he went again to Campeachy, where he acquainted himself thoroughly with the business of logwood cutting, in which he proposed to advance his fortune; for which purpose he returned to England in 1678. While in Campeachy, he became acquainted with some Buccaneers, who gave him an inclination for that kind of life, in which he was afterwards engaged, but of which in the sequel he became much ashamed.
He returned from England to Jamaica in April 1679, intending to become a complete logwood cutter and trader at the bay of Campeachy; but changed his mind, and laid out most part of what he was worth in purchasing a small estate in Dorsetshire. He then agreed with one Hobby to make a trip to the continent, before returning to England. Soon after commencing this voyage, coming to anchor in Negril bay at the west end of Jamaica, they found there Captains Coxon, Sawkins, Sharpe, and other privateers, with whom all Mr Hobby’s men entered, leaving only Mr Dampier, who also at length consented to go with them. This was about the end of 1679, and their first expedition was against Portobello. This being accomplished, they resolved to cross the isthmus of Darien, and to pursue their predatory courses against the Spaniards in the South Sea. On the 5th April, 1680, they landed near Golden Island, between three and four hundred strong; and carrying with them sufficient provisions, and some toys to gratify the Indians, through whose country they had to pass, they arrived in nine days march at Santa Maria, which they easily took, but found neither gold nor provisions, as they expected.