Cultural heritage is the creative expression of a people’s presence in the past. It represents a driving force to create, develop, and consolidate the sense of identity, belonging, and citizenship, as well as a means to appreciate the diversity of people and develop a policy for peace and mutual understanding. Furthermore, heritage is a source of economic development and a key factor for sustainable development. The dissemination of such values among people and the transmission of heritage to the future generations entail putting into the field proper actions, from the knowledge to the protection and conservation, and from the enhancement to the fruition and management. Such requirements increasingly involve the use of Information and Communication Technologies (ICTs) that can be considered the paradigm shift to create novel job opportunities in the field of cultural heritage. This paper aims to discuss an experience led by the Institute of Archaeological and Monumental Heritage of the (Italian) National Research Council (IBAM-CNR), with students of a secondary school of the Basilicata region (Southern Italy). The experience developed within the framework of the School-Work Alternation (SWA) (recently renamed “Pathways for Transversal Competences and Orientation” by Italian law), a training modality envisaged in the Italian school system to bring the school closer to the world of work by proper partnership between formal education contexts and external organizations. The SWA Project revolves around the acquisition of some technical and methodological tools for the approach to knowledge, conservation, and enhancement of cultural heritage, having particular regard for diagnostic tools and ICTs. This article deals with the outcomes of the activities developed during the Project, discussing both the technical-professional and transversal skills acquired or expected to be acquired by the students. In addition, starting from the results of the activities, the authors speculate about possible outlooks of SWA in the heritage field considering: (i) the role of such a training path in raising young people's awareness to preserve cultural heritage by becoming active and proactive citizens; (ii) the relationship of SWA with regional and European-supported development policy strategies; (iii) the potential benefits that SWA can provide for cultural heritage from the synergy between different institutional actors.