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Abstract: The literary works of Giuseppe O. Longo (three novels, ten collections of short stories, and one of theatre pieces) contain many references to the city of Trieste, as seen both in its topographical features and as an idesl place, a setteng for painful sensation, ripples of the soul, thrils and inner changes. As the extensive quotations contained in the paper illustrate, quite often the two planes, external and internal, overlap and entangle, giving rise to a transfigured city, imbued with a powerful symbolic and oneiric change. Everything is transformed by the author’s personality and obsessions, in a continuous crossing from reality to dream, in spite of the precision of the descriptions. If one is to understand Longo’s Trieste, so different from the literary commonplaces about that city, one should not limit oneself to the literal aspects, rather has to look for, and accept, the mass of implications connected to dreams, sex, disease, pain, fate, all themes around which a kind of complicated and evocative hypertext is entwined, often hallucinant and whirling, aiming at exploring the complex mystery of human existence, always in balance between concreteness and transcendence, between everyday deeds and the quest for the absolute. Amid intermittent gusts of the bora.