The current research aims at investigating how to promote better relationships between infrastructure and cultural heritage, with a more general objective to improve new ways to access and effectively use the places that are located in the surrounding landscape of infrastructure. Methodological aspects, related to the integration of GPS and GIS technologies, as tools to investigate territorial structure, have been applied to the territories in between Turin and Milan. Particularly the research combines a “top-down” approach, based on GIS density analysis, with a “bottom-up” approach, based on GPS tracking technology. Density maps show, through a visual technique based on the color scale, the distribution of “heritage areas”in the surrounding of infrastructure. GPS tool, based on mobile devices, has been used as surveying tool that allow to track, record and map new landscape structures, such as “cultural routes”, that can represent the real connection between infrastructure and cultural heritage. Cartographic representations, maps and schemes show, in a very effective way, the research outcomes at local and territorial level.