During this expedition, he noted a potential site for settlement as "Whitsun Bay" and a nearby hill "Mount Aldworth" after two of his merchant financiers in Bristol.
Returning to England in 1621, Pring was made a member of the Virginia Company and granted land in the Chesapeake Bay area.
In 1603, under patronage of the mayor, aldermen and merchants of Bristol, including Richard Hakluyt, Pring at the age of 23 was appointed as captain to command a ship and bark to explore the northern parts of the territory known as Virginia in North America and assess its commercial potential, financing it against a return cargo of sassafras.
Heading west, they visited the mouths of the Saco, Kennebunk and York rivers, all of which Pring found "to pierce not far into the land.
Anchoring the Speedwell at the lower harbour, Pring boarded the smaller Explorer and, aided by oarsmen, ascended the Piscataqua.
Pring must have been anticipating hostile (or unwanted) Native activity because his party brought with them on the Piscataqua "two excellent Mastives [sic]", one of which "would carrie a halfe-Pike in his mouth".
[11] Salisbury suggests that it likely had to do with the abrupt conduct of the English, insensitivity to local customs (which they used only when convenient), and their brutal use of the dogs against the indigenous peoples.
Subsisting on a variety of fish and game, Captain Pring's men harvested sassafras trees for export to England.
Pring escaped the poor fate of Leigh's party by abandoning the venture by catching an Amsterdam ship back home.
[13] Lord Chief Justice John Popham (judge) appointed Pring to make a second voyage to North America and assess the Maine coast in 1605.
In the Sunda Strait near to the Sumatra coastline, he met three more English ships of another fleet, which had been pursued by the Dutch from Java after having set anchor there.
Pring decided to send 3 ships north and to proceed to Japan himself to gain needed repair and provisions for the fleet.
With another 2 English ships, the Elizabeth and the Bull, he sailed to Japan on 23 July 1620, docking at Hirado Island, the only trading access allowed to foreigners.
He made contact with the factor Richard Cocks and departed Japan carrying the will of the recently bereaved EIC employee, William Adams on 26 December 1620.