This chapter tackles the debate on the role of sustainable tourism as a possible means to promote social innovation in peripheral rural areas. According to this perspective, the organization of the local tourist offer could be an opportunity to address social problems related to territorial and economic marginality, aimed at improving the livability of the towns. The issue is addressed in both theoretical and empirical terms through the analysis of the role of young entrepreneurs that have invested in innovative projects in pursuit of their “own life.” A state-of-the-art theoretical review about the tourist transition in peripheral areas is provided, and the results from fieldwork in Southern Italy are presented in order to offer the readers a more descriptive overview. The methodology is based on a case study research design and organizes the results according to both quantitative data of the tourist offer and qualitative data collected from participant observation and interviews with local tourist entrepreneurs and administrators. The findings show the impact of the changes in terms of increase in the offer of beds as well as in the development of a more open culture of hospitality within the local communities.