This paper aims at reassessing the concept of peripherality of the Byzantine insular world. It is suggested that Sicily, Crete and Cyprus (and to a lesser extent Malta, Sardinia and the Balearics) acted as a third political and economic pole between the Anatolian plateau and the Aegean Sea in the Byzantine Mediterranean. This will shed “archeological” light on some parallel economic and political trajectories of the urban centers located on two of the abovementioned islands: Salamis-Constantia on Cyprus and Gortyn in Crete during the transition from Late Antiquity to the Early Middle Ages.