In conditionally automated vehicles, drivers can engage in secondary activities while traveling to their destination. However, drivers are required to appropriately respond, in a limited amount of time, to a take-over request when the system reaches its functional boundaries. In this context, Virtual Reality systems represent a promising training and learning tool to properly familiarize drivers with the automated vehicle and allow them to interact with the novel equipment involved. In this study, the effectiveness of an Head-Mounted display (HMD)-based training program for acquiring interaction skills in automated cars was compared to a user manual and a fixed-base simulator. Results show that the training system affects the take-over performances evaluated in a test drive in a high-end driving simulator. Moreover, self-reported measures indicate that the HMD-based training is preferred with respect to the other systems.