This work reports the experience on the design and deployment of a WSN-based system for monitoring the productive cycle of high-quality wine in a Sicilian winery. Besides providing the means for pervasive monitoring of the cultivated area, the project described here is aimed to support the producer in ensuring the overall quality of their production, in terms of accurate planning of interventions in the field, and preservation of the stored product. Wireless Sensor Networks are employed as the sensing infrastructure of a distributed system for the control of a prototypal productive chain; nodes have been deployed both in the field and in the cellar, where wine aging is performed, and data is collected at a central unit in order to perform inferences that suggest timely interventions that preserve the grapes’ quality.