The question of the interactions between humanities and the digital world is receiving growing attention. Considering Italy through the lens of the digital humanities can bring about a fresh perspective on the “Italian question”, touching on issues of identity and history. Digitalization has sparked a cultural transition, paving the way for new fields of research. A number of Italian actors, both public and private, are engaged in redefining the issue of man vs. machine. For instance, in Italy as elsewhere, debates have emerged about the dangers of technology, focusing on the protection of freedom and human rights. The digital humanities therefore appear as an extremely interesting field through which to study the evolution of Italian society. Building a bridge between the digital humanities and Italian studies can open up teaching and research opportunities in both fields.