The integration of shared mobility modes into the transportation systems of European cities is continuously growing, providing an alternative option for sustainable mobility. Being implemented mostly in urban environment of Europe’s context, the peculiarities of an island are not taken into account in the frame of any research and policy recommendations available. The aim of this paper is to investigate the drivers and barriers for shared mobility on the scale of an island during both the planning and the operational phase, especially focusing on the North Aegean Region. The identification of factors that enable or hinder the adoption/success of shared systems on an island, as well as the respective conclusions were based on the methodological approach that capitalizes the stakeholders’ perspective. For this purpose, an interview was delivered to 15stakeholders of the Region while the development of the Analytical Hierarchy Process (AHP) allowed for a systematic evaluation of critical parameters that affect the implementation of shared mobility. This method compared with the results of the current mobility status of the island as well as the gaps that are identified by the stakeholders provided very interesting insights of the research. Results suggest that prioritizing technological advancements and enhancing user comfort can significantly boost the acceptance and efficiency of shared mobility services while confirm the need for different approach and adaptation of shared mobility aspects to the peculiarities of an islandic context in order to ensure the operational sustainability.