This article explores the relationship between wandering and everyday life in Simone (2012), a novel by the Puerto Rican writer Eduardo Lalo. Wandering, defined as an aimless movement around the city, is not only an instance to reflect and discover by walking the everyday life, but also to express a critical perspective towards the structures of power that articulates the daily life of San Juan. If the everyday relates to all daily activities, wandering is a representative movement of the rhythm of the city, which also enables to reveal the subversive potential of the everyday. Considering the figure of the flâneur, this article will analyze the way in which wandering is an instance to perceive the elusive and fragmentary nature of the everyday, which traces an emotional cartography of the postmodern city. Moreover, in the context of globalization, this aimless strolling has the potential to reflect on the non-places of everyday life. Finally, from the perspective of psychogeography, the article proposes that wandering in Lalo’s novel provides a critical view on the ideological dimension of everyday life, and particularly on its monotony and alienating effect.