The authors discuss wine tourism activities in the context of general tourism development in Slovenia. The country’s winegrowing areas have developed traditionally important viticulture, a relatively intensive production of typical grape varieties and in some cases also a distinct entrepreneurial spirit, which consequently reflects in tourism and regional development, based on diverse cultural heritage and natural values. Three Slovene wine regions are divided into nine wine districts with their own identities and more or less distinct terroirs. Despite a several centuries’ long tradition and a rich wine culture, it is evident that in national tourism strategies and development plans, wine tourism still does not occupy the position that it probably deserves, although most of the documents stress its potential for local or regional development. On the other hand, the authors recognize a significant interest among winemakers and tourism professionals for strategic cooperation and systematic approach to develop wine tourism in the selected destinations. The authors therefore focus on some paradoxes and emphasize examples of good practice at the national, regional, and local levels.