The spatio-cognitive properties of urban surroundings must be taken into account in the design of urban spaces. However there are few methods and software tools to assess the visual properties and the spatial identity of places, and most of them are based on two-dimensional visibility analysis only and on a static analysis of surroundings. Our proposal aims to provide turnkey solutions that could increase the implementation of urban planning policies concerned with sensitive impacts of urban fabric renewal. The method presented in this chapter enhances the urban space partition proposed by Peponis et al. (1997) in order to qualify all pedestrian paths in the studied area taking into account the importance of changes in visual surroundings and the vertical landmarks. In our use case, the results of our method applied on two paths are compared with a 3D isovists analysis in order to clearly show the keypoints in the path. A software solution has been developed as a plugin of the well-known SketchUp computer-aided architectural design (CAAD) tool to be tested by students in the context of project teaching in School of Architecture.