The study investigates the approach to collaboration in Humanities, within the Italian context, to test the possibility of collaborative digital library for scholars. The research hypothesis is that collaboration can foster innovation and scientific development: therefore, within Humanities, digital libraries can be the collaborative laboratory for research. Thus, understanding perception of scholars towards collaboration, especially online, and comprehending if wiki systems could be the framework of collaboration were the objectives of the study. A qualitative approach has been adopted, using case study as research method: five in-depth, semi-structured interviews to Digital Humanities scholars provide data integrated with interviews with two key informants (one of which is prof. Umberto Eco). The results of the study show that Humanities, within Italian context, do appreciate collaboration and the concept of a collaboratory digital library, though several issues need to be solved. In fact, Humanities are still tied with individual work and collaboration is not easy to pursue, for cultural, technical and political reasons. Great effort needs to be done at many different levels to eliminate obstacles and facilitate online collaboration for scholars. The study provides a draft model for a collaborative digital library arisen from gathered data.