This chapter offers a postcolonial feminist reading of the works of the British-Italian travel writer and adventuress Freya Stark (1893–1993), who travelled extensively throughout the Middle East and North African region. Her impact on travel writing as an unmarried European woman traveler, at the beginning of the twentieth century, without income, local connections or colonial rank is notable. This chapter provides close reading, through a postcolonial feminist lens, of two first edition volumes of Stark’s autobiographical travel books written during 1928–1939. The analysis explores the commercial nexus of Orientalism, which is the term that refers to Western depictions of the ‘Eastern’ world (Said E, Orientalism. Pantheon, New York, 1998). It discusses Stark’s work in relation to conceived reader expectations, as well as her distinctly ambivalent attitude to British colonialism and colonials. I suggest that Stark’s ambiguous role, as insider-outsider both within and between the Arab region and British Empire, poses provocative questions about the interrelationships of gender, self and ‘Other’ within commercialized Orientalist discourse (Ballaster R, Fabulous orients. Oxford University Press, Oxford, 2005). Stark makes specific discursive moves, not only as a traveler across continents, but in literary, ethnographic and gender terms. These moves manage to disrupt fixed framings, images and descriptions of Arab people, places and gender practices. This chapter therefore makes a unique contribution to theorizing Stark’s work and, also, travel writing more generally, locating it as an import discursive genre that is always underpinned by moving practices of gender, politics and power.