Meaning changes in tourism and new connections between territory and enterpriseResearch on tourists’ motivations and attitudes in Riviera Romagnola put into evidence that individuals are no more influenced from particular senses of belonging to a class or a cetus; they tend to follow more ephemeral orientations and belongings, which are connected to some elective groups. Today, tourist choice is more articulated and less predictable than before. This trend implies a new challenge for tourist entrepreneurs; most of them began to work in a mass tourism context, and now they feel alone, without any orientation model. In this contribution, we want to show some results of a research we did about local tourist entrepreneurs, in order to focus on how they perceive such change, and how they are planning some strategies to accomplish the new demand trends; at the same time, the research considers how entrepreneurs’ strategies are keeping or developing a corporate social responsibility for the local community.