Speaking about the creative heritage of Grigorii Skovoroda (1722–1794), the author considers the principles and results of his translation activities. A thinker of the 18th century, he translated classical authors (Ovid, Horace, Virgil, Cicero, Plutarch), and neo-Latin poets (Marc Antoine de Muret, Sidronius Hozjusz). Skovoroda not only translated, but also reflected on the principles and methods of translation. He recommended to take into account the peculiarities of the language and not to limit oneself with rendering the bare meaning of words. He also clearly distinguished between the literal translation (translatio) and free interpretation (interpretatio). In most cases, Skovoroda himself certainly preferred interpretation, because for him the translation was another way to express his own ideas. It is within the framework of such translation strategy that the philosophical principles of the thinker were realized. “Truth without beginning” was a fundamental idea for Skovoroda. That led not only to the Christianization of the works of Greek and Roman authors, but also to the Hellenization of Christianity. The author of the article on a number of specific examples shows how such translation strategy works in Skovoroda’s translations of Plutarch’s “De senectute” and “De tranquillitate animi” of Cicero.