This chapter provides a comprehensive examination of the intertwined challenges that, on the one hand, pose a threat to the resilience of wine tourism, whilst on the other hand, prevent the sector’s further development. The study, conducted in the Greek context, is based on personal, in-depth interviews with 39 key stakeholders and national experts. Thematic Analysis was used to interpret the qualitative data and identify prominent themes in participants’ responses. Specific stress factors were grouped into three main categories (i.e., economic, social and environmental), laying the basis for the development of an integrative resilience framework for wine tourism.