Smith is reputed to have killed and beheaded three Turkish challengers in single-combat duels, for which he was knighted by the Prince of Transylvania and given a horse and a coat of arms showing three Turks' heads.However, in 1602, he was wounded in a skirmish with the Tartars, captured, and sold as a slave.
After the four-month ocean trip, their food stores were sufficient only for each to have a cup or two of grain-meal per day.
Due to swampy conditions and widespread disease, someone died almost every day.
He then was taken to the Crimea, where he escaped from Ottoman lands into Muscovy, then on to the Polish–Lithuanian Commonwealth before traveling through Europe and North Africa, returning to England in 1604.
In 1606, Smith became involved with the Virginia Company of London's plan to colonize Virginia for profit; it had been granted a charter by King James.
By the summer of 1607, the English colonists were still living in temporary housing.
The search for a suitable site ended on when Captain Edward Maria Wingfield, president of the council, chose the Jamestown site as the location for the colony.
He was knighted for his services to Sigismund Báthory, Prince of Transylvania, and his friend Mózes Székely.
When Jamestown was established in 1607, Smith trained the first settlers to farm and work, thus saving the colony from early devastation.
As Smith describes it: "we all sold for slaves, like beasts in a market".
Smith claimed that his master, a Turkish nobleman, sent him as a gift to his Greek mistress in Constantinople, who fell in love with Smith.
Smith's books and maps were important in encouraging and supporting English colonization of the New World.