In the seventeenth century, Guarino Guarini, mathematician and architect, affirmed that architecture, a discipline that primarily deals with measures, relies on geometry: therefore, the architect needs to know at least its basic principles. On behalf of Guarini's words, we designed a set of interdisciplinary teaching experiences, between mathematics (via a calculus course) and drawing (via our Architectural Drawing and Survey Laboratory courses) that we proposed to first-year under graduate students studying for an Architecture degree. The tasks concern mathematical and representational issues about vaulted roofing systems and are based on the use of physical models in conjunction with digital tools, in order to make the cognitive geometric process more effective, thus following a consolidated tradition of both disciplines.