The Divine Comedy of Dante Alighieri, and its initial part of Inferno, includes several medical terms and descriptions, whose accuracy sometimes overcomes that of a layman. The genial poet has used locutions illustrating pain and sorrow more than forty times in Inferno alone, with words like dolor, dolente and doloroso, that have caused perplexity among translators. The panoply of translations – here we are dealing only with the English versions – will prove that not only the contextual meaning but also the historical setting might create interpretative difficulties. Without obviously giving medical value for granted to all verses that include words like dolor and its derivates, however Dante’s work has been as well under the focus of medical scholars, with many publications of interest. Through comparing the original text mainly with the Oxford’s English version, we have tried to bring into the reader’s attention the painful sensations that Dante abundantly inflicted upon his characters, as an indirect way to test the poet’s perception of this strange and infernal sensation