This article addresses the dispute between Greece and Turkey concerning the reach of their sovereign rights and jurisdiction in the Eastern Mediterranean, which is essentially about delimitation of the continental shelf and exclusive economic zone (EEZ). Turkey has delineated its continental shelf in the region to extend directly to the outer limits of the territorial waters of the Greek islands, specifically Crete, Rhodes, and Kastellorizo. Greece sees this as an attempt to deprive the islands of their maritime zones. The present article discusses what the two states might expect if they would request the International Court of Justice (ICJ) to determine the course of their maritime boundaries. The outcome of such a process would be difficult to foresee because international case law regarding the effect of islands on the delimitation of the continental shelf and EEZ is rather diffuse. Nevertheless, this article will explore what an equitable solution could look like. In particular, the small island of Kastellorizo, Greece’s most remote outpost in the Eastern Mediterranean, which lies just off the Turkish coast, requires special consideration. The present article discusses different options for dealing with this island in a future delimitation.