We investigated and modeled the temporal evolution of motion sickness in a highly dynamic sickening drive. Slalom maneuvers were performed in a passenger vehicle, resulting in lateral accelerations of 0.4 g at 0.2 Hz, to which participants were subjected as passengers for up to 30 min. Subjective motion sickness was recorded throughout the sickening drive using the MISC scale. In addition, physiological and postural responses were evaluated by recording head roll, galvanic skin response (GSR) and electrocardiography (ECG). Experiment 1 compared external vision (normal view through front and side car windows) to internal vision (obscured view through front and side windows). Experiment 2 tested hypersensitivity with a second exposure a few minutes after the first drive and tested repeatability of individuals’ sickness responses by measuring these two exposures three times in three successive sessions. An adapted form of Oman’s model of nausea was used to quantify sickness development, repeatability, and motion sickness hypersensitivity at an individual level. Internal vision was more sickening compared to external vision with a higher mean MISC (4.2 vs. 2.3), a higher MISC rate (0.59 vs. 0.10 min−1) and more dropouts (66% vs. 33%) for whom the experiment was terminated due to reaching a MISC level of 7 (moderate nausea). The adapted Oman model successfully captured the development of sickness, with a mean model error, including the decay during rest and hypersensitivity upon further exposure, of 11.3%. Importantly, we note that knowledge of an individuals’ previous motion sickness response to sickening stimuli increases individual modeling accuracy by a factor of 2 when compared to group-based modeling, indicating individual repeatability. Head roll did not vary significantly with motion sickness. ECG varied slightly with motion sickness and time. GSR clearly varied with motion sickness, where the tonic and phasic GSR increased 42.5% and 90%, respectively, above baseline at high MISC levels, but GSR also increased in time independent of motion sickness, accompanied with substantial scatter.