Zagora is a region located at the crossroads of Central and Northern Dalmatia, separated from the coastal area by a mountain range. The region has been facing numerous development challenges for decades, such as depopulation and ageing of the population, weak economy, and relatively poor transport development. A detailed overview of the demographic and economic characteristics of the region will provide a basis for identifying key challenges in modern economic development, as well as potential for future development. In order to gain deeper insight into the developmental issues of Zagora, a questionnaire survey was conducted among the local population and interviews were carried out with relevant participants in regional development. The results allowed the highlighting of the key advantages of living in Zagora, as well as ways in which these advantages can be utilized in the future. In addition, a cluster analysis of settlements based on demographic characteristics and transport accessibility to central services confirmed spatial differences in development characteristics within Zagora. This gives rise to the question of whether Zagora, in the modern times, can utilize the advantages emerging from the traits of rural landscape, a strong sense of belonging to the area, and the increasing population density of the coastal area.