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Macau, the world’s largest casino hub with the largest gambling revenues, has received increasing attention as a research focus. Macau attracts more and more Chinese outbound tourists each year due to its gambling industry monopoly in Greater China. Macau is positioning itself as a ‘world center of tourism and leisure’ and has set out plans to become a broader-based tourist destination with economic diversification. Thus, an understanding of people’s varied motivations plays an important role in the current status of an environment with a moderate diversification of economic development. The objective of this study is to classify the outbound mainland Chinese tourists in Macau into more homogeneous subgroups on the basis of their travel motivations. Thirteen motivation items are extracted into four factors (namely knowledge and culture, relaxation, entertainment and gambling, and prestige) through exploratory factor analysis. Three distinct market segments are identified—freedom seekers, multi-purpose seekers, and fun and special interest in gambling seekers—based on a cluster analysis using k-means methodology. This study also presents the socio-demographic and trip characteristic differences among these three segments.