In the Autumn of 2021, the Italian Regional School Office (USR) for Sicily launched the Insieme project with the aim of supporting schools and teachers in the development of learning environments and inclusive teaching strategies and to systematize groups and practices for self-evaluation of inclusiveness. Three Scuole Polo per l’inclusione participated in the first phase of the project, which took place during the school year 2021-2022: the Istituto Comprensivo Antonio Ugo in Palermo, the Istituto Comprensivo Italo Calvino in Catania and the Istituto Comprensivo Gesualdo Nosengo in Petrosino. Within each Institute, three classes identified by the Headmaster were involved according to selection criteria agreed with the USR. This article describes the aims of the Insieme project, the activities carried out in the first phase, the results achieved so far, the way forward in the next school years. The observation perspective is that of a critical friend who follows and analyzes the progress of the work, indicating its strengths and areas for improvement.