The translation of some works that belong to a different historical phase and a rather ancient culture require a doubled effort to adapt the translated text to the modern language and the target culture In his translation of Dante Alighieri's Vita Nuova, recently published in Cairo, Egypt, the author was able to identify some translationological problems in rendering Italian text into modern Arabic. This paper attempts to address these problems and explain the technical solutions the author adopted in his translation, which he believes can solve these problems. In his translation of Dante's the author believes that Dante's Vita Nuova is a literary text that requires a very particular treatment, especially hermeneutic and interpretative, which consequently leads to the confirmation that some literary works will always need to be manipulated in translation.