Drawing on twenty years of scholarship and translation experience, Emily Wilson—renowned translator of Homer’s Odyssey and Iliad —explores the difficult choices that translators must make, the pleasures of finding new solutions to old problems, and the inevitable frustrations of never fully capturing what is in the original work. Across chapters that range from the politics of Helen of Troy to the obscenities of Aristophanes, from Roman imitation of Greek models to contemporary debates over “foreignizing” and “domesticizing” translation styles, Wilson examines how modern norms of gender, sexuality, violence, humor, and power complicate our readings of ancient works, and how translation always risks denaturing what is unique and strange about the ancient world. Brilliant, erudite, and yet accessible to readers with no classics background, Crossing the Wine-Dark Sea is at once an introduction to the wonders of Greek and Roman literature, a manifesto for the value of translation in a rapidly changing world, and an invitation to encounter ancient cultures anew.