This monograph offers a comparative analysis of insularity within the legal orders of Italy, Greece, Spain, and France, and within EU law, arguing that Mediterranean insularity constitutes a juridically autonomous category with a historically stratified constitutional identity, deserving distinct recognition under European public law beyond purely functional approaches. Its analytical core is the diachronic relationship captured in the maxim ubi insula ibi ius speciale between insular condition and autonomist claims across the Mediterraneans principal islands. Mediterranean insularity differs from its North Atlantic counterpart in its deeper historical-cultural stratification, the primacy of geography over language, and the particularly strong link between self-government and insular identity. This emerges in Article 119, sixth paragraph, of the Italian Constitution on insular cohesion, in proposals for Corsican constitutional autonomy framed through Mediterranean insularity, and in the established frameworks of the Balearic and Canary Islands.