This study aims to understand the growing importance of the community from the perspective of cultural sustainability associated with living heritage. A case study associated with a cultural and natural border area between two municipalities located in the central region of Portugal is presented, following a quantitative analysis methodology. The experiences validated by the enjoyment of endogenous heritage resources and practices (material and immaterial), combined with natural ones, show the vital role that communities can play, as dynamic tourist practices that aim not only at territorial development, but cultural sustainability. Despite witnessing a growing interest in these dynamics found between tourism and the community(s), the study seeks to understand the relationship between tourists’ appropriation and cultural experiences on the cultural and natural dynamics of the community in the context of sustainability, culture, and tourism. This study contributes to the literature on cultural sustainability, observing forms of action that favor territorial development through the interconnection of the community, living heritage, and the territory’s resilience.