This essay reads Homer's Odyssey alongside several poems by the Greek-Alexandrian writer C.P. Cavafy who, although widely removed from the epic in time, shares a common geographical imaginary located in the Mediterranean and explores questions of cultural identity, memory, and gender in ways that resonate with the Odyssey's own preoccupations. The conceptual framework used to bring these poets into dialogue draws from ancient skepticism as a posture or way of being in the world that shapes philosophical and literary works bound up in what the Pyrrhonists called “the searching way.”

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