In 1598, the gentleman Anthony Sherley, an adventurer from a family of the English gentry and educated at Oxford University, set off on a reckless mission of unimaginable geopolitical importance: to reach Safavid Persia. Elizabethan England, opposed by the great Catholic powers and interested in forging relations with the Ottoman Empire - so far with little success - looked with interest to the Middle East. Since the annexation of Portugal in 1580, Philip II of Spain had monopolised the eastern maritime trade. The Sherley family was part of the faction of the Earl of Essex, a fierce opponent of Spain, whose aim was to extend English influence to counter Spanish maritime dominance. Essex's goal was an Anglo-Dutch coalition, to which Safavid Persia would be attached, able to rival Spain, Portugal and the Ottoman Empire. This, however, ran counter to the pro-Ottoman policy at the court of Elizabeth I. Sherley, without an official mandate, set out to forge an alliance with Shah Abbas I, a reformist ruler and skilful strategist. Leaving Venice in May 1598, the gentleman arrived at Abbas's court in Qazvin, the Safavid capital. Abbas, eager to break the Ottoman encirclement, welcomed Sherley warmly and offered him a daring task: to return to Europe as his ambassador extraordinaire to seek allies against Constantinople. Sherley accepted enthusiastically and was bestowed with honorary titles (including the Persian title of mirza, reserved for princes) and provided with official letters to European courts. As Jerry Brotton recounts, this meeting was emblematic of an England that was more global than the traditional narrative suggests: the Mediterranean and the Middle East were not distant borders, but vital theatres of diplomacy and alliances. However, Sherley's diplomatic project encountered many obstacles. Back in Europe, he found the courts wary; even in London, Elizabeth I, careful not to irritate the Ottoman Empire, was wary of this project of an anti-Ottoman Euro-Persian alliance. Elizabeth's successor, James I, definitively scrapped Sherley's plans, as his only goal was peace with Spain. Sherley ended the last years of his life as an exile in Spain, although the echo of his adventures deeply influenced the Elizabethan imagination.