This chapter examines Pietro Della Valle's travel narratives related to his visit to Istanbul (1614-1615) during his voyage to the Ottoman Empire, Persia, and India. It focuses on the Ottoman capital; its architecture, including mosques, mausoleums, palaces, and kiosks related to the sultans and dignitaries that Della Valle covered extensively in his travel accounts; as well as other "curiosities." Della Valle's self-fashioning through his pilgrimage of curiosity reveals the identity and the milieu of this Ronian nobleman who styled himself as it pellegrino (the pilgrim). His travel to Turkey in the early seventeenth century coincided with the reign of Sultan Ahmed I, a time when Europe and the Ottoman Empire were redefining their relationship. Published in the 1650's, Della Valle's Viaggi, describing his travels, was widely disseminated throughout Europe. The essay analyzes how Della Valle connected the European/Italian and Ottoman worlds through myriad boundary crossings as a cultural mediator, translatoi; and transmitter during a time of transition from the Renaissance to the Baroque age. The chapter's conclusion suggests that Della Valle's travel accounts not only communicated the Ottoman World to European audiences of his time but also played a significant role in shaping European perception of the Ottoman Empire in the eighteenth century, before the introduction of Orientalism.