This case study examines the business model of Capri Moonlight/Agricola Celentano, a wine company operating on the island of Capri, illustrating how it embodies resilience by deftly balancing centuries-old winemaking traditions with modern challenges. Despite wine production maintaining its fundamental process for millennia, contemporary issues, particularly climate change, necessitate a new sustainable approach from farming to packaging. The case highlights the company’s commitment to innovation without sacrificing heritage. Capri Moonlight/Agricola Celentano integrates organic and sustainable farming practices and explores new fermentation and ageing techniques, all while retaining traditional methods such as hand-harvesting and small-batch production. This dual commitment ensures their wines remain relevant in a changing global environment while preserving the island’s rich viticultural history. The chapter demonstrates that the ability to adapt to evolving environmental and market conditions, alongside a deep respect for tradition, is key to building a resilient business model in the face of modern challenges, showcasing Capri’s wine industry as a testament to adaptability and endurance.