This article provides a practical example of the development of cross-border tourism and its link to achieving sustainable development goals. Greenways (GWs) are successful and recognized initiatives in Western Europe, but have recently also shown development trends in Eastern Europe, notably, in the Baltic Sea Region and Russia. These initiatives improve the quality of life and provide opportunities for sustainable economic activities for the local communities, especially in rural areas, adding value to their natural, cultural, historical and human heritage. The authors studied examples of best practice in scientific literature and practice, encouraging the development of cross-border tourism and GWs in Europe and Russia, in order to further adapt it to other continents. Analyzing the environmental, economic, social and institutional factors in the region and their role in sustainable development, the need for institutional regulation that would allow the development of a wider development of GWs is identified. Research results reveal sustainable development dilemmas of positive socioeconomic effects of GWs and negative environmental effects of increased flows of tourists. Focus groups and expert interviews allowed us to assess the level of various factors contributing to sustainable development and clarify the directions of the future research.