This article offers a detailed investigation of Byzantine and post-Byzantine perceptions of the political organization of the Italian city-states. Drawing on philosophical and historical writing produced by Byzantine and post-Byzantine authors between the thirteenth and seventeenth centuries, it identifies the main patterns and motifs that informed Byzantine discourse about the constitutional arrangements of such Italian cities as Genoa, Venice, Florence, and Milan. It shows how these come into play in the writings of major figures of Byzantine and post-Byzantine intellectual life such as Theodoros Metochites, John Kantakouzenos, Nikephoros Gregoras, George of Trebizond, Cardinal Bessarion, Laonikos Chalkokondyles, and John Kottunios. It also explores the ways in which the classical legacy of political thought was applied by Byzantine writers in their analysis of various constitutional forms. The findings of this survey provide new insights into cross-cultural exchanges between the Byzantine world and medieval and early modern Europe and the formation of Byzantine identity.