This paper examines certain aspects of Maximus Planudes’ translation of Ovid’s double Heroides. Planudes’ intention is to remain close to the Latin original, however despite the overall satisfactory result his translation presents some problems. Omissions, additions, variations and stylistic features of his translation are discussed along with possible different readings of the MS that he used for his translation. It is further suggested, on the basis of stylistic and linguistic evidence, that Planudes’ Heroides translation antedates his translation of Ovid’s Metamorphoses.