In the study of figures of speech, similes have received far less attention than metaphors even though they are also frequently employed devices. This paper tries to contribute to the body of knowledge dealing with similes in English with special emphasis on the problems they pose in translation (from English into Italian). To do so, the first three sections respectively address the following issues: (i) the nature of similes in comparison to metaphor, as well as the various functions they can fulfill according to the genre in which they are employed; (ii) the different criteria used to classify them (e.g. objective vs. subjective similes, literal and non-literal comparisons, etc.); and (iii) the recognition and interpretation of similes. In turn, section 5, the core of this study, presents a detailed analysis of a number of examples from different textual genres pointing out not only the problems that arise in the translation of similes, but also, detailing the strategies that can be adopted to solve challenging instances. Some of these strategies, which Pierini applies to 'conventional' similes (e.g. "This meat is as tough as old boot leather") and 'encyclopedic' similes (e.g. "She did not like Carry Nation"), include the omission of the simile, literal translations, the replacement of the vehicle with another, the replacement of the vehicle with a gloss, etc.