This study explores the relationship between proximity and urban well-being, by combining qualitative and quantitative analyses of emotional perceptions of happiness at the neighbourhood level with an investigation of physical factors that measure spaces accessibility, services functionality, and citizens’ social perceptions. The main goal is to enhance ongoing research on the Smart, Close and Happy City to create a “Global Index for Measuring Urban Well-Being”, beginning with the human-scale “15-minute city” model. This research emphasises the need for an interdisciplinary approach that addresses the methodological gap present in traditional literature, which tends to separate the spatial analysis of urban infrastructures from the study of social dynamics. The methodology used for the overall assessment of neighbourhood proximity and urban well-being combines objective data with the subjective perceptions of users of the urban space regarding proximity, safety, comfort, well-being and spatial appreciation. The application of the adopted method on the San Benedetto (CA) neighbourhood highlights the importance of connecting the physical and emotional dimensions in evaluating the design effectiveness of a human-scale urban context.