This dissertation examines the Elaphiti Islands, an archipelago closely connected to medieval Ragusa, within the scholarly framework of island-mainland relations and Mediterranean networks. The islands are well attested in archival documents and are rich in medieval material remains. They preserve fifteen churches dated from the 9th to the 13th century, as well as architectural traces of settlements. By examining art-historical, archaeological, archival and literary sources, I reconstruct the islands’ living conditions in the 13th century, their relationship with Ragusa, and their role in the social, economic and artistic networks of the wider Mediterranean. Like many small islands in the Mediterranean, the Elaphiti Islands have been always examined through the lens of destitution and exploitation. Yet, the 13th-century sources from the rich Archive of Dubrovnik indicate that the islanders had a great deal of agency, and the number of churches condensed in this small area suggests that the islands were inhabited by industrious communities. The forms of these churches are an amalgamation of local styles and broader Mediterranean trends. Their architecture and decoration find parallels on the proximate mainland, but also in monuments in southern Italy and the Ionian and Aegean Seas. The close examination of the Elaphiti monuments, coupled with the uncovering of the islanders’ agency has made it possible to place the islands in a new strategic context. Situated at the gateway into the Mediterranean basin, with Byzantine territories to the east and Italian cities to the west, these islands, I argue, were actors in commercial and artistic exchanges in the Mediterranean, benefitting from their location on a permeable border between cultures and a watery boundary between political hegemonies.