Ground Penetrating Radar (GPR) is a flexible and cost-effective tool for performing structural integrity assessment and quick damage evaluation of manmade structures, including cultural heritage (CH) assets. In this context, this paper deals with the usefulness of GPR surveys enhanced by the use of a Microwave Tomographic data processing approach as a methodology for the diagnosis and monitoring of CH exposed to climate events and natural hazards. Specifically, the paper reports on the results of a measurement campaign carried out at the Loggia of the Consoli Palace of Gubbio (Italy). These results allowed us to increase our knowledge of the architecture of the surveyed zones and their structural hazards.