The nexus of changes in personal technology and human behavior has created new opportunities to understand cities by mapping the large-scale movements of goods and people through the use of GPS and GIS. Examples now abound making use of these technologies at the large-scale; we have chosen to look more carefully at individuals in cities. Our research has produced initial detailed studies from which more general urban behavioral and space syntactical patterns begin to emerge. We present two case studies that use food as a proxy resource relative to behavior. Our data collection methodology included both digital and traditional techniques, and our evolving analytical methodology draws upon visualization, interview-based observations and statistical analysis to offer qualitative and quantitative observations.