As the social phenomenon that takes into account cultural venues and facilities and cultural participation and attractiveness, the cultural strength of a city is a significant dimension of each city relevant for its inhabitants, as well as its visitors. The results of a research study on the nature of the relationship between cultural strength, on the one hand, and reputation and tourism intensity, on the other, are presented in this paper on a sample of the 20 European cities with the best reputation index according to the report entitled “The World’s Most Reputable Cities” (2018 City RepTrak®). The primary goal of the study is to determine the relationship between the cultural strength and reputation of these cities. The secondary goals are focused on determining the relationship between cultural venues and facilities as a segment of cultural strength and tourism intensity. The methodology used in the study comprises: the definition and analysis of the city reputation concept, as well as the determination of the differences in comparison with the reputation of an urban tourism destination, the identification of the constituents of the cultural strength of the cities and their role in tourist attractions, and finally, the investigation of the nature of the relationship between cultural strength, on the one hand, and tourism intensity, on the other. In order to conduct the analysis of these relationships and their interdependence, correlation and regression analyses are used. One of the conclusions of the paper is that cultural venues and facilities are not connected with the reputation of cities, whereas the correlation regarding cultural participation and attractiveness is confirmed. The results of the study also show the most important “cultural venues and facilities” indicator in relation to tourism intensity. In terms of this and based on the obtained research results of the study, the role that cultural strength plays in positioning cities in stakeholders’ perception through the strategic process of the creation and management of cities’ reputation, as well as the tourism attractiveness of cities and a consequent increase in the number of tourists as important stakeholders and ensuring their satisfaction, are presented in the paper.