This chapter adopts an experiential approach to exploring urban space, grounded in a tactile and embodied practice of seeing and sensing what is expressed through art and culture. It explores the relationship between the city of Naples and its contemporary artistic practices, notably cinema and neomelodici music, through the lens by Benjamin and Lācis’ essay on Naples and Benjamin’s development of the Baudelairean figure of the flâneur. The modernist flâneur serves as an interpretive guide to navigating the multi-sensorial experience of the postmodern city. Porosity is introduced as both a theoretical construct and analytical tool that shifts attention away from dominant cartographic representations, embracing more expressive ways of capturing the layered complexity of urban life. From this perspective, Naples emerges as a site of cultural resistance and transformation, where the city is experienced through all five senses and reimagined through the everyday practices of its inhabitants.