This chapter considers the overhaul of Palermo’s outdated maritime infrastructure in the late sixteenth century, a project compelled by competing visions of the city’s own modernity. It focuses on the design and fortification of the Molo Nuovo, a monumental port constructed on Palermo’s undeveloped northern outskirts. Intended by the viceroyalty to catapult the city onto a global stage, the controversial project jeopardized the city’s sense of security and sense of self. Through a close reading of memoranda and correspondence penned by both municipal and viceregal authorities, the chapter reconstructs experimental proposals for the Molo Nuovo – some realized, others abandoned – produced by itinerant engineers who crisscrossed the Mediterranean in service of the Spanish Crown.