This paper describes a system for collecting and analyzing multispectral imagery to evaluate crop health and streamline vineyard management in small to medium-sized vineyards. The system consists of three main components: a sensor assembly with a multispectral camera, quadcopter with flight automation, and a web-based decision support information system for analyzing multispectral imagery. Multispectral imagery can provide a holistic view of crop health through the use of different indices. A widely used index is the Normalized Difference Vegetative Index, which uses red and near-infrared reflectance as a proxy measurement for plant health. The authors tested the system at a small vineyard located in Albemarle County, Virginia, to better inform vineyard management of existing problems and trends in primary crop and undergrowth. Preliminary findings indicate the value of using this indicator based approach for analyzing crop health in vineyards.