A multifarious relationship exists between cultural tourism and SMSTs. As early as the 19th Century, several SMSTs (especially in Europe) began transforming their cultural heritage into tourism attractions. Recently, communities worldwide have focused increasingly on cultural tourism as a strategy to cope with economic restructuring and major (geo)political changes. Despite these phenomena, few academics have explored the role and the dynamics of cultural tourism in SMTSs. Moreover, there is a tendency in many such communities to uncritically borrow approaches from larger cities without paying attention to spatial and historical contingencies, which may lead to widely divergent outcomes. In this chapter, we describe the transformation in recent decades of SMSTs into cultural tourist destinations digging into literature primarily from urban studies and tourism research. Although several best-practice examples exist, there are also many more instances of failure that can be explained because of factors such as varying accessibility levels, divergent governance systems, or different levels of innovation to name but a few. While several communities struggle to establish themselves as bona fide destinations, others have been experiencing the uncomfortable situation of being loved to death by too many visitors. Indeed, there are several SMSTs that have been overwhelmed by overtourism. The global pandemic of 2020-21 has exposed the vulnerability of many communities, which depend on tourism as a major driver of economic growth and has led observers to ponder whether we have arrived at a metaphorical fork on the tourism development road. We ask whether this is an opportunity to rethink the role of cultural tourism towards engendering a more resilient and, ultimately, sustainable approach for the development of such communities.