Grapevines are subjected to many physiological and environmental stresses that influence their vegetative and reproductive growth. Water stress, cold damage, and pathogen attacks are highly relevant stresses in many grape-growing regions. Precision viticulture can be used to determine and manage the spatial variation in grapevine health within a single vineyard block. Newer technologies such as remotely piloted aircraft systems (RPASs) with remote sensing capabilities can enhance the application of precision viticulture. The use of remote sensing for vineyard variation detection has been extensively investigated; however, there is still a dearth of literature regarding its potential for detecting key stresses such as winter hardiness, water status, and virus infection. The main objective of this research is to examine the performance of modern remote sensing technologies to determine if their application can enhance vineyard management by providing evidence-based stress detection. To accomplish the objective, remotely sensed data such as the normalized difference vegetation index (NDVI) and thermal imaging from RPAS flights were measured from six commercial vineyards in Niagara, ON, along with the manual measurement of key viticultural data including vine water stress, cold stress, vine size, and virus titre. This study verified that the NDVI could be a useful metric to detect variation across vineyards for agriculturally important variables including vine size and soil moisture. The red-edge and near-infrared regions of the electromagnetic reflectance spectra could also have a potential application in detecting virus infection in vineyards.