In light of its environmental diversity, and specialisation in grain, and to a lesser extent wine production, a thorough understanding of late antique Sicily’s local economies, and their connections with the broader Mediterranean exchange system, is a major desideratum in the current debate on the ‘long’ Late Antiquity. This paper draws upon the archaeological evidence available for the Sicilian interior and the fresh datasets produced by the Philosophiana Project in the hinterland of Piazza Armerina, particularly for the period A.D. 300–700 (with some reference to the 8th and 9th c.). It aims to analyse the reasons for Sicily’s marked late antique economic growth and settlement expansion. This article also tries to situate the economy of inland Sicily in the much debated context of central Mediterranean state-sponsored trade and free markets. This is so we can investigate how the close connections between the grain heartland of Sicily and Rome impacted on the complexity of local economies. Ceramic production and distribution are widely used to reconstruct the sophisticated system of exchange engaged by the island in the long term.