The study covers the geomorphological transformations of the area in which the city of Urbino rises, starting from the first Roman settlement, until reaching the nineteenth-century nucleus and the current situation. The design of the walled city and its immediate surroundings is analysed with GIS tools, that allow one to manage data in a georeferenced way, to evaluate the changes of urban expansions in the various historical periods and to represent them not only from a qualitative point of view but also a quantitative one. The representations of the analysis make use of all the 2D and 3D devices available for a greater understanding of the data analysed.