In off-pump coronary artery bypass grafting (OPCAB), the coronary arteries are joined as the heart beats. This procedure requires high skill and experience to be performed reliably and quickly. Although training kits are commonly used for technical training, the inability of trainees to always be with experienced surgeons for guidance and to receive immediate evaluation remains problematic. To address this problem, a system that allows a single trainee to observe and quantitatively evaluate the procedures performed by an experienced surgeon is being developed. In this study, to analyze the differences between the motions of experienced and novice surgeons, Leap Motion was used to measure the hand motion of the vascular anastomosis performed by both surgeons using a training kit. Using the measured data, the features of the vascular anastomosis surgical techniques performed by experienced and novices were tested using the Mann–Whitney U test. In addition, a binary classification was performed using machine learning with these features. The binary classification results show that trainees can be classified as experts or novices with high accuracy using the developed system.