In my paper, I reconsider the syngramma of Moschio reported by Athenaeus (Moschio ap. Ath., 5, 206d-9e = FrGrHist 575). The syngramma contained a large description of the Syrakosia, the great ship of king Hiero II of Syracuse (269-215 BC). This textual evidence was largely employed to reconstruct the artistic and technical culture of the Hieronian Kingdom, supplying for the lack of systematic surveys of material evidence that characterized the history of the study of this historical context. In addition, the description of the technical features of the Syrakosia was used in to the scholarship on technology in Ancient World. In the first part of my paper, I shall argue that the syngramma of Moschio does not describe a real ship but the city of Syracuse in an allegorical form. In the second part, I shall discuss the historical and cultural context in which this allegorical representation was formulated, and I shall argue that it is Syracuse at the time of Hiero. My argument is based on textual and material evidence related to the art of the court of Hiero, which is characterized by allusion and allegory, as the dynastic art of Ptolemaic Alexandria. In conclusion, I shall argue that this allegorical representation is an example of Hellenistic “mental cityscapes”: this “ship of city” is a way to imagine and represent the city very different of our geometrical and cartographical “mental cityscapes”.