This thesis applies the theoretical framework of City as Layers to investigate the interrelationship between urban memory, dwelling, and infrastructure, using the small coastal town of Polignano a Mare in southern Italy as a primary case. The research begins by outlining three contemporary urban predicaments—eroded collective memory, alienated dwelling, and fragmented infrastructural landscapes—and translates them into measurable and spatially observable dimensions. Through historical documentation, morphological mapping, and site-based experiential analysis, including a five-day diary structured around thematic observations, the thesis constructs a layered reading of the town’s spatial and cultural identity. Building upon this analytical foundation, six value propositions are formulated as key evaluative criteria for design.