In recent years, the integration of new media literacies and, consequently, strategies such as transmedia learning in teaching–learning processes has been a topic of interest among various types of national and international institutions and governments. In this sense, the current article deals with the abilities and habits of Italian students of licei classici (Italian classical high schools) to cope with these new formative contexts that are arising. For this purpose, different quantitative instruments (from the field of attitudes, digital skills and multitasking, and corresponding to the transmedia sphere) were administered to 400 students (N = 400). The results show that most young people have access to devices and that they prefer the mobile ones when consuming or creating content on the net. Moreover, although they are inclined towards transmedia practices, they have some difficulties in becoming creative agents collaborating and fully participating in digital citizenship.