Climate change is projected to be a key influence on crop yields across the globe. Regarding viticulture, primary climate vectors with a significant impact include temperature, moisture stress, and radiation. Within this context, it is of foremost importance to monitor soils’ moisture levels, as well as to detect pests, diseases, and possible problems with irrigation equipment. Regular monitoring activities will enable timely measures that may trigger field interventions that are used to preserve grapevines’ phytosanitary state, saving both time and money, while assuring a more sustainable activity. This study employs unmanned aerial vehicles (UAVs) to acquire aerial imagery, using RGB, multispectral and thermal infrared sensors in a vineyard located in the Portuguese Douro wine region. Data acquired enabled the multi-temporal characterization of the vineyard development throughout a season through the computation of the normalized difference vegetation index, crop surface models, and the crop water stress index. Moreover, vigour maps were computed in three classes (high, medium, and low) with different approaches: (1) considering the whole vineyard, including inter-row vegetation and bare soil; (2) considering only automatically detected grapevine vegetation; and (3) also considering grapevine vegetation by only applying a normalization process before creating the vigour maps. Results showed that vigour maps considering only grapevine vegetation provided an accurate representation of the vineyard variability. Furthermore, significant spatial associations can be gathered through (i) a multi-temporal analysis of vigour maps, and (ii) by comparing vigour maps with both height and water stress estimation. This type of analysis can assist, in a significant way, the decision-making processes in viticulture.