Nowadays, digital media play a central role in a shift towards updated modes of communicating knowledge. In addition to this, the tragic recent events related to the long series of earthquakes that have taken place in central Italy have also, unfortunately, reiterated the need to document and preserve not only the material value of the architectural heritage but also the intangible values related to the events and people that have characterized their history. In this framework, the paper investigates some of the opportunities offered by technological innovations, in particular, by the specific application areas of augmented reality and augmented virtuality. The historical site chosen as case study is the complex of Santissima Annunziata, which has played a very important role in the city of Ascoli Piceno (Italy) for centuries.