This study utilized generational cohort theory to enhance understanding of the motivation and destination image of Mainland Chinese tourists visiting Taiwan (i.e., cross-strait tourism). With 350 Chinese tourists traveling to Taiwan, unique characteristics of four generations were identified (e.g., the Republican generation was more highly motivated to visit friends and relatives than the other generations, the Social Reform generation had greater hedonic motivation for visiting Taiwan than either the Consolidation or the Republican generations). The inconsistent characteristics between cohorts could be attributed to generational differences in past historical experiences. Thus, findings suggest that an individual’s life experience could play an important role in forming an image of the destination where the experience is related to, and also suggest that cross-strait tourism, one of the unique contexts of quasi-states tourism between politically divided countries, has a strong generational component, and tourism policies between such countries must take this into account.