Dante Gabriel Rossetti is one of the main interpreters of Dante, both in literature and the visual arts; he translated Dante`s Vita nuova (as well as poetry by Dante`s contemporaries) into English and revived Dante`s literary world in his paintings. His interpretations were unique as his technique of painting. This is because he had no opportunity to have formal training in fine art. In fact, he was criticized for his technical immaturity in drawing and perspective which, ironically, led him to express his vision with more originality. However, more importantly, his originality needs to be traced to his absorption in Dante`s literary world, which, with its inexhaustible inspiration, had produced many, diverse adaptations. The relationship with Dante was crucial in order for Rossetti to establish his own way of expressing himself. This is because for Rossetti conveying symbols and meanings was much more serious than technique. In particular, we need to note that the originality of Rossetti`s vision did indeed derive from his contemplation of Dante`s literature; here the vision can be understood as that which Dante pursues in his pilgrimage toward salvation. This vision allows them to see the eternal value and truth beyond the superficial perception of things. This paper aims to read closely the paintings that Rossetti based on Dante and thereby show that his interpretations are indispensable for understanding the aesthetic value of Dante`s literature. As poet and painter, Rossetti created the so-called two-fold work of art in the way in which he includes Dante`s linguistic text in the frame of his paintings or writes it into the paintings directly. By this means he seems to have strived to show the reciprocal effect of saturation between word and image. His paintings are realistic in that they faithfully represent Dante`s world, in which Dante`s contemporary realities are inexorably related, and, at the same time, fantastic in that they always display symbolic and allegorical signification. He can be evaluated as a translator of Dante; here what translation means is something not only literary but also cultural insofar as, through his capacity of creative alteration, he promoted the alternative development of the language and culture to which he belonged.