This chapter aims to identify the possible routes that could be used to encourage creative tourists, particularly at heritage sites. It is based on in-depth interviews and observations conducted in George Town and Melaka, Malaysia’s World Heritage Sites, between March 2015 and May 2017. A total of 20 documents, including interview transcripts, field-notes, and textual documents were analyzed and used to discuss how different stakeholders or local communities could play roles in nurturing creative tourists. Applying the concepts of sense of place and action-oriented knowledge to these findings, possible alternatives for different stakeholders to nurture creative tourists are identified. The authors also articulate the challenges faced by these stakeholders and suggest future research for bridging the literature gaps encountered.