In ancient times, what guided ships and their fates was revered as Fortuna gubernatrix: the goddess of luck at the helm. However, when the Renaissance bestowed upon her symbols like billowing sails and falling dice, the old goddess of fate had become the figurehead of modern trade and exploration. She now symbolized nautical technologies and the knowledge of chance and fortune. From then on, Fortuna di mare became a technical term for all maritime dangers that imply active risk management. In this dual perspective of image and concept, metaphor and medium, the study reveals the sea as an open field for experimentation between technology and poetics, as a horizon of diverse passages between seafaring and literature.