A traveler to Florence is all eyes. This city at the center of Machiavelli’s political thinking is a world of architecture, sculpture, and painting. There is no choice but to embrace the visual. The student who encounters The Prince may not have walked through the streets of Florence, yet teachers of political theory can direct students to the visual aspects of his text. As a literary scholar interested in visual culture and a political theorist respectively, we propose an integration of iconographical and close textual readings. We model this multidisciplinary approach for the concepts of prudence, parsimony, liberality, and fortune by showing how the meaning of politicized concepts becomes intelligible through the study of allegorical images. We offer teachers a terminology for interpreting the text through its images. An embedded link offers access to a store of images relevant to the study of The Prince.