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Drawing on the evidence of the maps themselves, as well as the discourses surrounding them, the article argues for the existence of military cartography in the Middle Ages. Noting parallels between the reception of De re militari of Vegetius and the first descriptions of cartography clearly made for military purposes, it argues that the idea of using cartography in military practice emerged at the end of the thirteenth century. Land maps, like sea charts for the dangers of the sea, were considered as tools to help surmount the difficulties of a ground campaign and even to anticipate the outcomes of a broader strategic plan. Subsequently, numerous maps served military purposes in addition to other functions. It was in Italy, divided into independent states, engaged in continuous conflict, and during the Italian Wars, that one first perceives more systematic usage of maps. Contrary to what is often claimed, it is not possible to see in this process a “conceptual revolution” instigated by the influence of the Geography of Ptolemy, translated in Florence at the beginning of the fifteenth century.