This contribution mainly focuses on Cyprus and the Balearics, islands located at opposite geographical extremes of the Byzantine Mediterranean, during the passage from Late Antiquity to the early Middle Ages. Historians have often regarded these islands as peripheral additions to the Byzantine heartland of the Aegean and the Anatolian plateau; this article argues that, in fact, archaeological and material indicators (such as ceramics, lead seals and coins), paired with the scarce textual sources, point to a certain degree of economic prosperity in the abovementioned islands during the period under scrutiny, suggesting that they continued to play an important role in the political, administrative and religious structures of the Byzantine Empire. A resilient insular economy and continuity of local production of artefacts was ensured by the persistence of demand from local secular and religious elites and regular, if infrequent, contacts with other areas of the Byzantine heartland or the Muslim Mediterranean.