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Through the sixteenth and early seventeenth century, Italian architects, under the auspices of Philip II, transformed the Sicilian port of Palermo into a scenographic colonial stronghold. Regularized perimeter fortifications, monumental city gates, and diagrammatic arterial restructuring embodied Renaissance Ideal City models and concretized ephemera from Charles V’s triumphal entry of 1535. An extensive iconographic program proclaimed Habsburg imperialism, patronage, and religious piety. This paper examines a series of maps and city views from 1580 to 1700, wherein cartographers devised progressively more abstract images of Palermo as a quadripartite city, denoting an ideogram of an earthly paradise. Radically altering urban and topographical realities, cartographers crystallized the theoretical and metaphorical urban ideals envisioned by architectural planners. Parallels to the hermetic symbolism and evocations of the Garden of Eden, Solomon’s Temple, and the New Jerusalem, evidenced in Philip II’s Escorial, suggest the monarch’s critical role in shaping this idealized urban object from afar.