This thesis examines the complex relationship between reality and representation in maps, and how this relation has influenced the perception of the map and its ability to convey information throughout history. The study analyses historical maps of Venice and Amsterdam, highlighting their evolution from detailed depictions to simplified representations. Through philosophical theories and cartographic investigations, it reveals the paradoxical nature of map truthfulness, where distortion often becomes a means of communication. From the mythical portrayals of the historical city to the modern diagrammatic transit maps, this thesis traces the progress of cartography, examining how maps balance accuracy with purpose, ultimately prioritising coherence over correspondence with reality.