In a globalized and hyper-connected world, multiculturalism should no longer be considered a complicated process full of barriers. However, from the research conducted, it has emerged that in heterogeneous working contexts with collaborators from different areas of the world, managers encounter many difficulties in managing cultural peculiarities and differences. At the same time, schools, faced with the change constituted by the strong presence of foreign students, experience a strong need to fully understand the effects of multiculturality and to produce adequate and aware responses, in organizational and managerial terms. The P.Ir.A.M.iD. project, acronym for Path of Intercultural Awareness, Measurement and Development, intends to address these issues in both environments. The theme of diversity management calls into question identity issues, processes of categorization and social comparison and intercultural skills. In particular, one of the sectors in which diversity management can find a peculiar and relevant field of application is precisely the tourism sector. Intercultural skills in particular are indispensable for reading and managing situations. However, the development of intercultural competences is not yet included in an appreciable way in main training paths, especially in the sector of vocational education and training and of professional trainers.