The integration of new media literacies and, consequently, strategies such as transmedia learning in the 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, thoughts and expectations that Italian students in classical high schools have in order to face these new formative changes. For this purpose, a mixed methods approach (qualitative and quantitative) was designed and applied in the context of a classical high school in Cagliari (Italy): a questionnaire on digital skills (N = 128), a set of semi-structured interviews (N = 17) and two focus groups (N = 14). The results obtained allow us to verify that, from the point of view of skills, adolescents are prepared to take on the challenges of transmedia learning (navigation, information management), although their collaboration skills need to be strengthened. On the other hand, from the cognitive and affective points of view, they are positive and enthusiastic about these new possibilities: greater interaction, flexibility, engagement and variety of resources and learning strategies.