Wine is one of the world’s oldest and most culturally rich products — but it also offers a unique lens into how we classify, learn, and personalise experiences. In this talk, we’ll explore how the wine world is increasingly shaped by data and AI — from vineyard optimisation and market forecasting to taste profiling and personalised recommendations. We’ll also take a closer look at how algorithms approach a deceptively simple question: What wine will I enjoy? Using models like decision trees as metaphors, we’ll walk through how technology tries to learn human preferences — and where it often falls short. This session blends practical insights with a touch of humour and curiosity, offering both wine lovers and data enthusiasts a fresh perspective on what it means to make informed, intuitive decisions in a world of complexity.