Connectivity is a crucial issue for tourism development, especially in Mediterranean island destinations, whose accessibility from the mainland tourist origins depends entirely on sea and air passenger transport services. These operations are subject to significant market oligopolisation; therefore the study of the prevailing industrial configuration is essential. In this context, the paper argues that irrespectively of the initial conditions of location, market power in transport may affect significantly the territorial pattern of tourism flows in Mediterranean island destinations. More specifically, the spatial implications of the previous air and sea passenger transport regulatory regime in the European Union are compared with those of the present liberal framework to conclude that neither of these systems provides the ideal connectivity conditions in the Mediterranean as issues of core and peripherality are insufficiently addressed. From this perspective, the policymakers are advised to enrich the current deregulatory framework with a set of active tourism strategies based on solid foundations of industrial economics and island transport geography.