How do empire and its unraveling shape travel, its writing, and its images? To answer this question, my work examines late Ottoman and Turkish Republican travelogues about the Russian Empire and Soviet Union (and vice versa). In travel texts, perception and representation are closely intertwined with authorial and political power: specifically, with negotiations of the onto-epistemological status of both travelers and “travelees.” Consequently, travel accounts – with their active constructions of visited objects and of visiting subjects – present fecund opportunities for mapping continuities and ruptures between empires and their successors. I analyze the generation and maintenance of expansionist, imperialist-tinged discourse in four twentieth-century texts: Ivan Bunin’s “Ten’ ptitsy” (Bird’s Shadow, 1908), Celal Nuri’s Şimal hatıraları (Recollections of the North, 1912), Falih Rıfkı Atay’s Yeni Rusya (New Russia, 1931) and Lev Nikulin's Stanbul, Ankara, Izmir (Istanbul, Ankara, Izmir, 1935). As both Bunin and Nuri interrogate the prospects – if not feasibility – of Ottoman progress, they also highlight networks of exchange and influence belonging to one territory but located in the other. Even after the fall of empire, Nikulin establishes the Soviet Union’s cultural, creative, and industrial positionality over the Turkish Republic, while Atay maintains empire’s mimetic and diegetic registers through discussions of Soviet public space and cinema and through reprisals of Ottoman discourse on development. My work brings literary studies into dialogue with comparative Ottoman/Russian and Turkish/Soviet historiographies, specifically by assessing distinct deployments of imperiality and orientalism within and across literary traditions and cultural-political paradigms. Such attention helps identify consistencies and dislodgments in a textual corpus itself premised upon continual displacements while shedding light on the dynamic, if not volatile, relations that have existed – and continue to exist – between these two spaces.