Connectivity and isolation problems have become a source of policy interest in all European countries, largely as a result of the goal of the completion of the internal market. Against this background, the present paper aims to analyze the future position of the Aegean passenger shipping system. Thissystem will likely face major changes, caused by technological and political-economic factors. The driving forces and the subsequent implications ofthese future developments for the Aegean short sea shipping sector will be investigated. The analytical framework is based on a blend of forecastingmodelling and scenario experiments for the Aegean transport system. Consequences of international political-economic changes as well as new transport(de)regulations (such as hub-and-spokes systems or market contestability) are traced in the paper with a view on identifying feasible futures for theAegean maritime transport sector.