The following article aims to present the results of a research experience that defines a geographic information system oriented at the architecture of closed areas of cloisters and courtyards of the historic center of Ascoli Piceno. This experimentation is part of the scenery of documentation's activities for the management and the enhancement of urban environmental improvements through the use of integrated technologies closed and open source. Therefore the main object of the analysis was the architectural one, in its different, articulated and individual features, but always considered in relation to the same geographical location, in this case the urban space, consequently focused not only on the object itself, but also on the relationship between this and any other similar ones. In this sense, the tested geographic information system is intentionally hybrid. We wanted to check the possibility of binding different shape and nature data to the "map" by structuring in a well organized manner different information – drawings, videos, photos, 3D, etc.. – in order to realize a GIS that would allow to analyze the architecture of cloisters and courtyards both in its relations to the urban context and in its specific spatial qualities.