The unique memorable experiences provided to customers directly determine a business’s competitiveness. The extant tourism literature has provided limited explanation of the factors that characterize this memorable tourism experiences. Hence, this study is trying to address two purposes: first, to evaluate the motivating experience factors that leads travelers from different cultural origins to different preferences when selecting their travel destination, and second, to assess the respective relevance of the identified factors in the destination’s competitiveness. A mixed, electronic and paper-based survey, with a specific reference to the Mediterranean destinations, was conducted in a sample size of 156 travelers. A multiple chi-square analysis was performed to identify factors that lead to specific selections and to assess the relationship between culture group (Eastern vs. Western) and tourist experiences. Further analyses were performed to identify the predominant/primary reasons for differentiation in the selection of destination. The findings show cultural differences in the memorable experiences and the respective criteria that travelers use while selecting/reselecting a traveling destination. Finally, the study draws conclusions, provides some managerial implications, and suggestions for future work.