This essay investigates Goethe’s 1786–88 Italian journey in the context of the history of “getting lost”—from Greek epics, to fairy tales, to postmodernity—and asks: Why does Goethe get lost on purpose? What were the literary, psychological, and political stakes of this? And how does it relate to his apparent “discovery” of classicism? By comparing Goethe’s contemporaneous travel notes with his revisions for the 1816–29 publication, the author argues that Goethe deliberately repeats the Odyssean narrative of lost-and-found in order triumphantly to find himself, both psychologically and as a writer. Yet Goethe simultaneously demonstrates a strikingly sophisticated anticipation of modern theories of literature and travel. Realizing that he can never really lose himself—geographically, psychologically, literarily—he meditates on this impossibility and discovers the necessity of walking in others’ footsteps.