The goal of this on the road driving study was to investigate how drivers adapt their behavior when driving with conditional vehicle automation (SAE L3) on different occasions. Specifically, we focused on changes in how fast drivers took over control from automation and how their gaze off the road changed over time. On each of three consecutive days, 21 participants drove for 50 min, in a conditionally automated vehicle (Wizard of Oz methodology), on a typical German commuting highway. Over these rides the take-over behavior and gaze behavior were analyzed. The data show that drivers' reactions to non-critical, system initiated, take-overs took about 5.62 s and did not change within individual rides, but on average became 0.72 s faster over the three rides. After these self-paced take-over requests a final urgent take-over request was issued at the end of the third ride. In this scenario participants took over rapidly with an average of 5.28 s. This urgent take-over time was not found to be different from the self-paced take-over requests in the same ride. Regarding gaze behavior, participants' overall longest glance off the road and the percentage of time looked off the road increased within each ride, but stayed stable over the three rides. Taken together, our results suggest that drivers regularly leave the loop by gazing off the road, but multiple exposures to take-over situations in automated driving allow drivers to come back into loop faster.