The seismic vulnerability and damage assessment of heritage buildings at the regional scale can be considered a complex measurement problem that has suggested the development of specific multi-level procedures based on the inventory and classification of typological, constructive features, vulnerability parameters, potential or existing damage. Ancient masonry churches represent a particularly vulnerable architectural typology and the experience progressively acquired during post–earthquake observations have pointed out that recurrent damage patterns and main failure mechanisms can be identified by separately looking at the different architectural “macro–elements”, through on-site surveys. In the last few years, the macro-element approach has been extensively and fruitfully applied to perform preliminary vulnerability assessments, by recognizing the correspondence between each structural macro-element and the most recurrent collapse mechanisms associated. This paper deals with the measurement problem of damages to evaluate seismic vulnerability of historical masonry buildings. To this aim an information system is proposed consisting of a computer platform (named Quality Detection Platform - QDP) and a mobile device dedicated for data acquisition supported by Internet of Things (IoT) technology. The QDP evaluates a vulnerability index by using the macro-element approach and the Analytic Hierarchy Process (AHP) is used to improve the interpretations of the obtained measures and calibrate the relative importance of the kinematic and static criteria and automatically assign the weight to each mechanism.