We propose an automatic and non-invasive system for monitoring the health of vine plants by measuring their water stress, with the goal of mitigating the increasingly frequent extreme meteorological events such as droughts. The envisioned system measures the spatial distribution of the Crop Water Stress Index (CWSI) on the crop field, to provide the farmers with a precise control on their vine’s health and, therefore, on the final quality of their product. To ensure the robust acquisition of parameters needed to compute the CWSI, data are collected by field sensors on the ground, by drones, and by exploiting satellite data. Data fusion then allows to obtain an associated georeferenced heatmap of the vineyard. The solution has been tested via a prototype, which allowed the collection of information in a vineyard.