>Smith set off to sea at age 16 after his father died. He served as a mercenary in the army of Henry IV of France against the Spaniards, fighting for Dutch independence from King Philip II of Spain. He then went to the Mediterranean where he engaged in trade and piracy, and later fought against the Ottoman Turks in the Long Turkish War. He was promoted to a cavalry captain while fighting for the Austrian Habsburgs in Hungary in the campaign of Michael the Brave in 1600 and 1601. After the death of Michael the Brave, he fought for Radu Șerban in Wallachia against Ottoman vassal Ieremia Movilă.
>Smith reputedly killed and beheaded three Ottoman 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 Crimean Tatars, captured, and sold as a slave. He claimed that his master was a Turkish nobleman who sent him as a gift to his Greek mistress in Constantinople, Charatza Tragabigzanda, who fell in love with Smith. He then was taken to the Crimea, where he escaped from Ottoman lands into Muscovy, then on to the Polish–Lithuanian Commonwealth before travelling through Europe and North Africa, returning to England in 1604