This paper analyses the translation of figurative language in a novel by the American writer Richard Brautigan, titled So The Wind Won’t Blow It All Away (1982). Translating figurative language has been traditionally considered a particularly challenging and fascinating task, due to its interplay of linguistic and cultural associations, and it has often been seen as a borderline topic in translation studies. In this paper, my attention will be devoted to contextual factors and to the fact that, in a literary text, metaphors and similes reinforce themselves into a highly structured whole. Richard Brautigan’s novel offers a fertile ground of analysis in this respect, because of its rich imagery and its extensive and peculiar net of metaphors and similes. Drawing from my own Italian translation of this novel (American Dust: Prima che il vento si porti via tutto, 2005), I propose a close-reading of the text metaphorical patterns, in order to set in context the different figurative expressions and the different translation strategies adopted. The high degree of originality of several figurative expressions may indeed simplify the task of the translator, as some scholars argued, although the risk of undertranslation is patent when striking metaphorical language is used.