The paper evaluates the current status of tourism development in the Wine route region in Macedonia. It analyses the major problems and obstacles that prevent further tourism expansion of this region by pointing to weaknesses that need to be addressed. The main accent is put on the necessity for reformulating the strategy for change. A field survey was conducted in the line of assessing the up-to-date tourism growth. The overall conclusion is that the destination has profound limiting factors for further tourism development. Therefore, the current marketing strategy needs an improvement in the line to overcome the spotted obstacles for destination and product development.