The period known as the Italian Renaissance witnessed a rebirth of Greek learning and, along with it, a renewed impetus to translate the two epic poems, the Iliad and Odyssey, attributed to Homer in antiquity. During the course of one century (1362-1460s) there were more than a dozen attempts to translate Homer from Greek into Latin. These Latin versions were the first to be printed in the fifteenth century and in turn offered a template for the first vernacular translations well into the seventeenth century. In addition to translation practice, humanists also began to develop increasingly more sophisticated ways of thinking about the task of the translator and thus did much to advance the field of translation theory. Despite this decisive contribution to the history of Homer's reception and interpretation, critical commentary on the period as a whole has been largely negative. The argument of this dissertation is that much of the scholarship on Homer's reception in the Renaissance is still beholden to aesthetic assumptions inherited from the period in question. Chief among them is the assumption that translation can only take place between two texts (source and target) and that one of the most important features of a good translation is its fidelity to the source text, whether that be in word or sense. Additionally, scholars often expect a translation to stand alone as a piece of literature in its own right. Many humanists of the day and scholars thereafter held Homeric translations up to these standards and judged them a "failure." By applying a historical-contextualist methodology, I put pressure on the "failure thesis" by arguing that there was never any consensus about the standards to which translators ought to hold themselves; these standards changed over time; and in many cases they were simply impossible to fulfill. These translations can be divided into three phases: Literal ("The Feather") (1362-1440s), Oratorical ("The Wing") (1438-1460s), and Verse translation ("The Flight") (1440s-1500).