Human-centered approaches are of particular importance when analyzing urban spaces in technology-driven fields, because understanding how people perceive and react to their environments depends on several dynamic and static factors, such as traffic volume, noise, safety, urban configuration, and greenness. Analyzing and interpreting emotions against the background of environmental information can provide insights into the spatial and temporal properties of urban spaces and their influence on citizens, such as urban walkability and bikeability. In this study, we present a comprehensive mixed-methods approach to geospatial analysis that utilizes wearable sensor technology for emotion detection and combines information from sources that correct or complement each other. This includes objective data from wearable physiological sensors combined with an eDiary app, first-person perspective videos from a chest-mounted camera, and georeferenced interviews, and post-hoc surveys. Across two studies, we identified and geolocated pedestrians’ and cyclists’ moments of stress and relaxation in the city centers of Salzburg and Cologne. Despite open methodological questions, we conclude that mapping wearable sensor data, complemented with other sources of information—all of which are indispensable for evidence-based urban planning—offering tremendous potential for gaining useful insights into urban spaces and their impact on citizens.