The rapid development in low-cost sensor and wireless communication technology has made it possible for a large number of devices to coexist and exchange information autonomously. It has been predicted that a substantial number of devices will be able to exchange and provide information about an environment with the goal of improving our lives, under the well-known paradigm of the Internet of Things (IoT). One of the main applications of these kinds of devices is the monitoring of scenarios. In order to improve the current wine elaboration process, this paper presents a real-time monitoring system to supervise the status of wine casks. We have focused on a special kind of white wine, called Fino, principally produced in Andalusia (Southern Spain). The process by which this kind of wind is monitored is completely different from that of red wine, as the casks are not completely full and, due to the fact that they are not renewed very often, are more prone to breakage. A smart cork prototype monitors the structural health, the ullage, and the level of light inside the cask and the room temperature. The advantage of this smart cork is that it allows winemakers to monitor, in real time, the status of each wine cask so that, if an issue is detected (e.g., a crack appears in the cask), they can act immediately to resolve it. Moreover, abnormal parameters or incorrect environmental conditions can be detected in time before the wine loses its desired qualities. The system has been tested in “Bodegas San Acacio,” a winery based in Montemayor, a town in the north of Andalusia. Results show that the use of such a system can provide a solution that tracks the evolution and assesses the suitability of the delicate wine elaboration process in real time, which is especially important for the kind of wine considered in this paper.