The focus of the present paper is on the development of a methodological framework for guiding strategic decision-making towards the sustainable future development of peripheral small island regions, constituting distinct examples of lagging behind regions at a European scale. This will be implemented to a specific peripheral small island region, the island of Lefkada-Greece, seeking the integrated development of the island with emphasis on the sustainable exploitation of local tourist assets. The proposed framework is built upon the exploration of both the external and internal environment of such regions as well as the use of foresight and participatory evaluation tools. The study of the external environment aims at shedding light on the potential developments of the 'decision environment', within which policy making has to take place; and is framed by policy developments and tourist market trends ranging from the global to the national/ regional level. The analysis of the internal environment aims at gathering knowledge concerning the specific environmental, economic and social context of the study region, where the strategic planning exercise is addressed. Information gathered on potential developments of the external environment are used to inform the structuring and evaluation of sustainable tourist development scenarios in order to conclude with the most prevalent future perspective for the specific region, taking into consideration the local preferences and values in a participatory evaluation context. Finally, some conclusions are drawn, based on the experience gained from the application of the proposed methodological approach and the results obtained from the specific case study.