This article re-interprets the American photographer Walker Evans’s Havana portfolio from a perspective that combines psychology and geography. By taking this approach, the article intends to reflect further on a number of the photogra- pher’s developing methods and processes, which were implemented whilst docu- menting his visit to the Cuban capital. In this discussion a number of theoretical issues relating to the medium of photography emerge in a way that examines the relationship between photography and psychogeography. This is illustrated via an exploration of the photographer’s practice with reference to psychogeography itself and is developed with reference to the act of urban wandering and the figure of the flaˆneur. These inform the photographer’s visual understanding of the physical presence of the city, upon which he attempts to imprint himself in a way that is both involving and deliberately disassociative.