This chapter traces the maturation of Palermo’s architectural idiom across a network of local churches in the Kalsa and Loggia districts. Designed in collaboration with itinerant architects from southeastern Sicily and the Iberian Mediterranean, these early sixteenth-century monuments bear the mark of local builders and craftsmen fluent in ornamental and structural solutions inherited from the Normans. In Palermo’s contested cultural environment, building sites became laboratories for the development of a speculative architecture that tested the limits of architectural revivalism. Local practices of vernacularization and historicization developed against the backdrop of the city’s rich humanistic tradition, which creatively reimagined Palermo’s proximate and distant pasts.