In order to address the challenges of cultural diversity Italian schools are facing, new initiatives are required in teacher education. This chapter surveys a number of theoretical models to identify the level of intercultural skills of practitioners and proposes a new training programme designed to increase the intercultural skills of teachers and social workers working in multicultural contexts. The experiences of teacher education initiatives at the Catholic University of Milan confirm the programme’s initial assumptions: sensitivity, understanding, a critical reprocessing of personal experience and self-reflection (introspection) are all essential to improving the quality of intercultural skills training. The author argues that these assumptions are especially important in light of the increasing conflict and racism present in Italian schools today.