A cycling wheel chair (CWC) is a useful tool to provide physical exercise for patients who face difficulty walking, caused by stroke or other brain disorders. A system has been developed for rehabilitation, which allows patients to practice driving a CWC in a virtual environment. In this study, hardware improvements were developed and methods for evaluating driving skills were investigated to improve the practical application of this system. The hardware was changed to enable users to drive the CWC they were using in their daily lives. In addition, four types of test scenarios that focused on basic and important actions necessary to drive a CWC, such as pedaling and steering, were developed. An experiment with healthy young and elderly persons was conducted to evaluate the validity of the system. Results showed that pedaling and steering skills were improved in both the young and elderly subjects but the improvement patterns differed between them. These results indicate that repeated practice with the proposed system enhances the safety of driving a CWC, particularly for elderly users.