The wine as a cultural product become the main theme of tourism development in the most 14 wine regions in Portugal. The wine tourism can be established as a regional development tool, allowing the integration of the primary (agriculture), secondary (wine industry) and tertiary (tourism) sectors, highlighting the landscape attributes and showing the regional “touristic terroir” (Hall and Mitchell, 2002) singularities. The tourism and wine industries are increasingly identified as natural symbiotic partners (Carlsan & Charters, 2006, p.18) concerned about business and territories’ sustainability. This winwin relationship must be anchored on coopetitive networks, taking advantage of partnership skills and stakeholders’ synergies. In this study, the first objective was to characterize the complex wine tourism ecosystem starting with a deep literature review. The Enotourism Ecosystem is composed by 3 pillars, the Wine Culture, Territory /Landscape and Tourism, where the touristic experience is the heart of visitor encounter with the material and immaterial heritage. The second objective was to identify the main wine stakeholders and partnership intensity degrees. The third objective pointed to Enotourism critical factors, seeking business success and territory sustainability. To get primary information it was built an online questionnaire survey applied to 51 wine tourism companies (convenience sampling). The findings showed a complex relational interconnectivity between stakeholders within the ecosystem, a low number of units establishing partnerships and a soft cooperation level with other players and public/private entities. So, to get business success and territorial sustainability, it will be crucial that all stakeholders must strengthen their partnership relations, developing coopetitive value cocreation strategies.