The outbound tourism of China has drawn global attention recent years. With the capacity of over 57 million outbound tourists in China, Macao and Hong Kong constantly rank at the top two positions attracting over 70% of the Chinese tourists to these two Special Administration Regions (SARs). Macao, being a gaming destination, is renowned as “Las Vegas of the East”; whereas Hong Kong, being a non-gaming destination, is renowned as “World-renown Shopping Paradise”. Theologically, the perceived attractiveness and the travel motivations of both SARs should not be the same as the highlights and development of the tourism products are totally different. In addition, the gradual reform of tourism policies and the launching of the Individual Visit Scheme in China pave the way for the tourism growth for these two SARs of China. Therefore, understanding the travel behavioral differences of Chinese outbound tourists, the majority group of visitors coming to Macao and Hong Kong, is critical and can enhance significant contributions in future tourism-related studies. The purpose of this dissertation is to examine the behavioral characteristics of Chinese outbound tourists in term of travel motivations, non-gaming expenditure and sensation seeking propensity among four different groups i.e. Macao and Hong Kong as well as Gamblers and Non-gamblers. This is an exploratory study with a sample size of 1047. Respondents are Chinese outbound tourists choosing Macao or Hong Kong as travel destination. Data were collected through a survey questionnaire. The findings of this dissertation provide evidence that Chinese outbound tourists visiting Macao/Hong Kong emphasis on “Food”, “Sightseeing” and “Historical scenic spots/Cultural Heritage” when choosing travel destinations in general. Chinese outbound tourists visiting Macao are mainly for “Gambling” and “International Competitions/Events”. On the contrary, Chinese outbound tourists, who have high consumption on high-end and branded products, are mainly for “Shopping”, “Sightseeing” when visiting Hong Kong and “Transportation Efficiency” is found to be an important criterion for them. Though Macao is a gaming-oriented travel destination, she is able to attract both gamblers and non-gamblers. Besides, gamblers give high ranking on “Gambling”, “High-class hotel and entertainment facilities”, “Transportation Efficiency” and “International Competitions/Events” when visiting Macao/Hong Kong and their consumption is mainly on expensive/high-end products and entertainment. Results of this dissertation not only contribute much to the tourism industry with more in-depth understanding on the behavioral characteristics of Chinese outbound tourists toward these two SARs; but also help marketers to tailor their tourism products/services towards targeted customers and legislators to investigate effective and practical strategies boosting local leisure and gaming contribution in order to sustain their competitive advantages as well as driving other tourism-related industries moving forward.