This research contributes to literature on private sector adaptation, examining business-level adaptation to climate change in the UK wine sector. The research adopts a temporal and relational view of adaptation, through a sector-wide, value chain lens and through considering adaptation to both climate variability and longer-term change. Using the lens of ‘a good year’ and ‘a bad year’ in the sector, we consider the role of extreme events in adaptation decision-making and learning. We focus, unusually, on both opportunities and risks of climate change. Results show businesses increasingly see climate change as an opportunity for the UK wine sector. Yet climate risks remain and propagate along value chains, through supply and demand. This produces winners and losers in ‘good years’ and ‘bad years’, as well as over longer timescales. We find businesses along the value chain take steps to engage in extensive proactive adaptation behaviour, often right from business design and development. Business relationships condition climate risk exposure and adaptive capacity and adaptation decisions within one business can influence risks and opportunities throughout the value chain. Our results also reflect and develop organisational adaptation theories. We find businesses continually refine their adaptation strategies in response to climate variability and extreme events. They enhance adaptation learning by experimenting with new technologies and strategies. Irregular and extreme events can become important focal or tipping points in creative iteration and innovation of adaptation strategies, including for longer-term climate change. Our results stand in contrast to earlier literatures which suggest that businesses consider climate change to be too uncertain, or long-term, to engage in adaptation. Instead, climate change has become a master-narrative within the wine industry, through which sector actors often interpret their experiences and orient their business design and activities. Results indicate a strong dependence on own experience in adaptation decision making, that risks creating adaptation lock-in. We propose a typology of proactive private sector adaptation responses.