Smart tourism has already become an important part of the worldwide tourism development. The article provides a comprehensive analysis of the international practice of establishing and developing Smart cities, based on scientific and methodological research. It demonstrates that cities with a high degree of digitalization are becoming a driver of the intensification of tourism. It is important to analyze the degree of digitalization of Smart cities, taking into account economic and cultural factors in symbiosis with digital ones. The purpose of the study is to identify the possibility of developing Smart tourism in cities with different levels of digitalization. The article analyzes tourists, the business community and the city administration as the main stakeholders in the level of digitalization of the city for developing of Smart tourism. Based on a retrospective analysis and comparative study of existing global indexes assessing the digitalization of cities, new criteria have been identified that seem essential for the Smart tourism development. These criteria were divided into 4 categories: tourism business activity, ecological measures, Smart experience, infrastructure, and each identified a set of metrics that are most important for sustainable development. It is proposed to use 4 groups that differ in the level of digitalization based on the methodology of point-rating benchmarking. Based on the proposed criteria and point-rating benchmarking, Moscow and St. Petersburg are analyzed as one of the main tourist Smart cities in Russia, and Abu Dhabi and Beijing as important points of global tourist attraction. Conclusions are drawn about their level of digitalization and development prospects. The application of proposed methodology will allow authorities at all levels to identify priority areas of support for Smart cities, identify and eliminate problems in the field of tourism digitalization, as well as form effective public–private partnerships with investors.