Wine Routes develop inside the larger context of wine tourism (WT), which is increasingly important for rural communities. Italy is one of the most important countries in the world for wine production and tourism. Sicily is one of the leading regions in Italy for wine production and wine tourists. This study focuses on the Sicilian wine routes (SWRs) and gives an excursus of their development during the last ten years, highlighting strengths and weaknesses. Moreover, the study wants to make an attempt to bridge the existing gap in the literature and highlight the nature and extent of the contribution of the SWR to the development of the WT ‘product’ from the perspective of the increasingly booming sustainable–rural tourism. Face-to-face interviews were conducted along the SWRs with 283 wine tourists, 65 wine enterprises, and eight expert stakeholders. The motivations for tourists to visit the first time and their intention to return were investigated by the explorative factor analysis. Moreover, the wine tourist profile was highlighted. Findings outline some specific features of the general experience economy model where visitors’ emotional involvement and local cooperation appear crucial for the integrated territorial development of the backward rural areas of wine regions in different parts of the world. Managerial implications of findings are discussed.