In this study, we used Urry’s concept of "tourist gaze" to examine social construction of tourism in Singapore based on a case study in the Chinatown. This social construction was formed by interactions of three major stakeholders the public sector, the private business sector and the tourists who come from abroad. The Singapore Tourism Board had adopted a series of policy measures to induce tourists from abroad by building sightseeing space through image marketing and festival planning. In the development of tourism industries, the local people were increasingly concerned about the issue of disappearing "authenticity" which was evidenced in the Chinatown. However, international tourists seemed not to be affected by such transformation. The study did some interviews with Taiwanese tourists of the E-generation and found out that this cohort are more knowledgeable of the Nanyang style and exotic Chinese "traditional heritage" symbols. By collecting these differentiated symbols the tourists could recognize the sightseeing process they are experiencing. Furthermore, study also found that there were embedded political, social and economic values in the policy measures the Singapore government adopted in promoting tourism.