Cellar doors provide retail sales for wineries, providing higher returns than wholesale to domestic and export markets. Customer-based research has established enjoyable cellar door experiences are essential to building brand attachment, creating enduring customers, and increasing on-site and post-visit sales. However, customers co-create cellar door experiences with staff, as each approach the experience with unique realities guiding their expectations. Scarce literature includes experiences from staff perspectives. Constructivist grounded theory and adopting Charmaz’s approach to analysis were used to explore data from semi-structured, in-depth interviews with 33 wine consumers ranging in wine involvement, from wine novices to highly involved enthusiasts and winemakers. Twenty-two of the consumers were cellar door staff with experiences ranging from a few months to owners of long-established family wineries. Cognitive dissonance theory helped us to understand how tensions may arise for individuals approaching each experience and where to avert perceived risks. Findings show convivial connection respecting all actors creates enjoyable experiences. The warmth of greeting, further strengthened by staff–customer rapport, developed via knowledgeable conversation throughout the experience, increases brand attachment. Co-created connection becomes the conduit through which positive experiences are created and where brand attachment is forged. A framework based on emerging categories guides professional development models and human resources strategies for wineries, thereby maximizing profitability through cellar door sales.