Research in aviation and driving has highlighted the importance of training as an effective approach to reduce the costs associated with the supervisory role of the human in automated systems. However, only a few studies have investigated the effect of pre-trip familiarization tours on highly automated driving. In the present study, a driving simulator experiment compared the effectiveness of four familiarization groups, control, video, low fidelity virtual reality (VR), and high fidelity VR on automation trust and driving performance in several critical and non-critical transition tasks. The results revealed the positive impact of familiarization tours on trust, takeover, and handback performance at the first time of measurement. Takeover quality only improved when practice was presented in high-fidelity VR. After three times of exposure to transition requests, trust and transition performance of all groups converged to those of the high fidelity VR group, demonstrating that: a) experiencing automation failures during the training may reduce costs associated with first failures in highly automated driving; b) the VR tour with high level of interaction fidelity is superior to other types of familiarization tour, and c) uneducated and less-educated drivers learn about automation by experiencing it. Knowledge resulting from this research could help develop cost-effective familiarization tours for highly automated vehicles in dealerships and car rental centers.