The success of Macao as an international gaming hub is ironic, considering that the government has rarely promoted it as a gambling destination. Rather, government marketing and promotional efforts promote Macao as a world heritage destination, which raises questions about marketing efficiency, the effectiveness of tourist segmentation, and the allocation of marketing resources. This in-depth investigation compares visitor types by probing whether gaming visitors participate in activities similar to those undertaken by cultural heritage visitors and vice versa. The goals of this article are twofold: to assess the degree of compatibility between divergent visitor segments in a destination based on their behavior and propensity to undertake different activities, and to gauge the implications for long-term sustainable and effective tourism marketing efforts. This is in contrast with previous studies, which in general consider only segment attractiveness and focus mostly on just one unique visitor segment. In addition to the activities sought, this article examines the level of involvement and social characteristics of both gaming and cultural heritage visitors.