In this paper, we conduct parsing experiments on Dante Alighieri’s Divine Comedy, an Old Italian poem composed between 1306-1321 and organized into three Cantiche —Inferno, Purgatorio, and Paradiso. We perform parsing on subsets of the poem using both a Modern Italian training set and sections of the Divine Comedy itself to evaluate under which scenarios parsers achieve higher scores. We find that employing in-domain training data supports better results, leading to an increase of approximately +17% in Unlabeled Attachment Score (UAS) and +25-30% in Labeled Attachment Score (LAS). Subsequently, we provide brief commentary on the differences in scores achieved among subsections of Cantiche, and we conduct experimental parsing on a text from the same period and style as the Divine Comedy.