The aim of this paper is to demonstrate the power of the new digitization technologies and, in particular, of Virtual Reality (VR) to document and communicate the knowledge of Cultural Heritage (CH) and to shorten the distance between man and his history, enhancing architectural monuments or art masterpieces (even when they are somehow inaccessible), allowing original educational storytelling and producing innovative ways to learn and enjoy culture. The ultimate goal of this research is the virtual and interactive reconstruction of an important historical site, characterized by a great beauty as well as by a high artistic value: the complex of Santa Maria delle Grazie, in Milan. In order to test an effective digitization workflow, the experimentation focused on the areas of the convent that are closer to the church and that have been characterized by a troubled history: The Cloister of the Frogs, the Cloister of the Prior, the Old Sacristy, the Small Sacristy and the New Sacristy. These environments have been surveyed by combining photogrammetry and terrestrial laser scanning; then they have been modelled as NURBS or reconstructed in the form of meshes. In the end, the entire 3D model was imported in a game engine in order to create a realistic VR simulation, able to revive the convent’s history in a way that no written document could better explain.