This article aims to show how the Divine Comedy can be an important support for the Teaching of the Catholic Religion in schools. The starting point is Pope Francis’ exhortation to become Dante’s companions on the journey. To make explicit the reasons that support this invitation, the article offers an overview of the Poet’s life, emphasizing with the help of other literary figures the richness of his human experience and his ability to reread his own life from a theological perspective. It is then proposed to make these insights more concrete by limiting the analysis to two central themes of the Comedy: love and freedom. Through the reading of passages selected from Cantos XVI, XVII and XVIII of Purgatorio, and Canto V of Inferno, a great affinity of issues and expressions peculiar to our days is highlighted, and a presentation is made of how Dante resolves conflicts within an integral Christian vision of man, his feelings and his transcendent aspirations.