In the context of the global COVID-19 pandemic, the world of cultural heritage has had to cope with the closures of museums and dedicated structures. In this dramatic context, the digitisation of assets represented a partial solution to guarantee the fruition of the world’s cultural heritage. Even in the context of teaching, the pandemic represented a challenging moment. This contribution presents three different university teaching experiences focused on lighting for cultural heritage. The workshops described were held before, on horseback, and amid the pandemic. The differences are contextualised in the Italian regulatory and methodological framework. Attention is also paid to the digitisation of assets regarding the lighting design verification of the students’ project proposals. The teaching approach, the procedures, the material presented by the students, and the revision methodology are described. The comparison between the three editions allows for evaluations of the main problems encountered in the different contexts and when the used procedures were instead strong points. The use of three-dimensional simulation, initially designed exclusively for lighting verification, has also proved crucial in the communication of students’ works, demonstrating once more that in the future, the information technologies will be able to help those who deal with cultural assets to expand the catchment area and to enhance the communication of sites and museum structures.