The tension between tourism and heritage has existed for a long time. From practical-based understanding of heritage, most literature concerned with management issues attempts to interpret the relationship between heritage and tourism. Tourists are routinely defined as causing economic commodification, pollution, and physical damage to sites, and they obscure or erode other values of heritage. Most importantly, tourists have been defined as “culturally inauthentic” and as passive sightseers, with little or no agency in the meanings they construct at heritage sites. However, several authors argue that although tourists may bring negative effects, they are also mindful and actively engage in constructing heritage-meaning during their visits. One of the key issues of tourists using heritage is related to their emotional and affective features in the fields. This paper explores the idea of emotional empathy and its role in the expression of different forms of heritage in the context of Southeast Asia with respect to two Chinese cultural world heritage sites—the West Lake Cultural Landscape of Hangzhou, and the Ancient Villages in Southern Anhui: Xidi and Hongcun—and is based on fieldwork. Firstly, I discuss whether tourists are simply passive receivers of an “authorized heritage discourse,” or whether they play a more active and thoughtful role in understanding the meaning of their visits to heritage sites. I argue that tourists are engaged in multi-dimensional empathetic processes during their visits to heritage sites. Those processes may be shallow and banal, or may be intense with deep emotional engagement. Nevertheless, they are actively constructing contemporary heritage meanings. Secondly, I discuss the complex interactions between local communities and tourists. I argue that locals also experience such empathetic processes when they feel their daily lives have in-depth linkages to tourists. During the empathetic processes, material heritage is a “living theatre” where both locals and visitors generate a sense of empathy and interact with each other. Heritage, therefore, is a place where people feel—and in particular connect—to something vital, notably to other people or to land and ancient times.