The idea of the pentarchy directly expressed by Justinian I (527-565) – Novella 131 – is also perceptible in cartography. This paper examines the 41 medieval and early modern world maps in the context of the vignettes of the pentarchy. From the above analysis shows that almost every map from this period had a vignette of Jerusalem and 37 maps have a vignette of Rome. But only 28 maps have a vignette of Alexandria, 24 maps have a vignette of Constantinople, and 20 maps have a vignette of Antiochia. In the case of Jerusalem, a huge majority of vignettes is a sacred buildings (most often it is the Tomb of Christ). Only in three cases is a Holy Cross. In contrast, Rome’s vignettes represent both religious buildings and fortifications. As for the drawings on the vignettes of Antiochia, Alexandria, and Constantinople, the vast majority of them are character of fortifications. These vignettes are, on the one hand, a close relationship with the history of these cities, on the other hand, they are associated with the medieval and early modern politic ideology and theology. This paper is trying to capture and analyze these complicated, religious, political, and theological relationships, and explaining the meaning of these vignettes.