In this article, we address the issue of poetic translation and re-translation, beginning from a theoretical approach and, then, contextualizing it by the Italian versions of Antonio Machado’s poetry during the 20th century and the last decades. In the first part, we underline the most important elements that make poetic (re-)translation an autonomous, creative and original “literary genre”. In the second part, we compare Machado’s translations by Oreste Macrì to the ones newly realized by the author of the present article in terms of language, strategies and editorial target.