Joseph Woory was a member of the English expedition that set out from Charles Town on June 16, 1666, to explore the area from Cape Romano (Cape Fear, called Cape San Romano by the Spanish) down to Port Royal. The expedition took 26 days, during which time they visited St. Helena Island, where they saw a large wooden Spanish cross, Edisto, and Kiawah Island. Woory wrote about the rich quality of the soil, the different kinds of vegetation, varieties of fish and fowl, and Indian fields planted with corn, peas, and beans. The explorers visited Indian villages at Edisto and St. Helena, where they left behind one of their company, Henry Woodward, to learn the Indian language. Woory reported that the Indians were friendly and "seemed very willing to have us settle amongst them." The company sailed from Port Royal on July 9 and arrived at Charles Town on the 12th.
In 1663, Charles II gave large land grants in what is now North and South Carolina to eight men who had supported his restoration to the throne in 1660. Almost immediately, William Hilton was sent by the proprietors to explore the area. His favorable reports attracted emigrants from New England, who arrived at the end of 1663 to form a small English settlement in what is now North Carolina on the west bank of the Charles River (later named Clarendon River, now Cape Fear River), about 20 miles upstream. The colonists did not like the location, and abandoned it after a few months. In May 1664, John Vassall settled the area with a second English group, this time from Barbados, but the proprietors encouraged the settlers to explore more territory to the south in order to find a better place for a permanent settlement. Lt. Col. Robert Sandford was chosen to command the expedition of 2 small vessels, the Speedwell and the Rebecca. They set out for the southern coast on June 16, 1666, and returned on July 12, a month later. Though the settlers remained at Charles Town until 1667, lack of supplies and hostilities with the Indians led to eventual abandonment of the tiny colony.