The way in which the towns of Enna, Agrigento and Trapani were considered in modern iconography was quite different. Enna was not included in the 16th century Atlas of towns and was only of minor interest for the Grand Tour. On the contrary, Agrigento, although quite well known between the 15th and 16th centuries, due to its importance as a wheat producer, can be found in the iconographical inventories only in the late 1700’s, as European travellers had, in the meantime, extended the range of their wanderings southwards in search of antiquities. As a flourishing emporium between the Peninsula and Africa, Trapani begins to be featured in collections of portraits of towns at the end of the 1500’s. It then gained great notoriety over the following centuries, just as its political and economical role in the kingdom was becoming marginal. Only with the growing phenomenon of travel in Sicily do urban portraits finally manifest significant changes in the choice of the perspective and of the issues to be highlighted.