Objective The current study investigated the factors that predict drowsy drivers’ decisions regarding whether to take breaks versus continue driving during long simulator drives. Background Driver drowsiness contributes to substantial numbers of motor vehicle crashes, injuries, and deaths. Previous research has shown that taking a nap and consuming caffeine can temporarily mitigate drowsiness and enable continued safe driving. Method Ninety drivers completed a 150-mile highway drive in a driving simulator after a day of partial sleep restriction. Drivers passed several simulated rest areas where they could take breaks. To replicate drivers’ motivation to reach their destination safely but also quickly, drivers were told that they would be paid more for completing the simulated drive faster but would forfeit their payment if they crashed. Results Break taking was predicted by drivers’ self-ratings of drowsiness and by the severity of lane departures. However, even at the highest levels of drowsiness, most drivers bypassed simulated rest areas without stopping. In comparing self-rated drowsiness to drowsiness measured by eye closures, drivers often under- and over-estimate their own level of drowsiness. Conclusion Drowsy drivers use their own self-assessed drowsiness when deciding whether to take breaks. These self-assessments are often incorrect, and even when drivers rate themselves as severely drowsy they are unlikely to stop to rest during long drives. Application The findings reveal the need for effective drowsy driving countermeasures to motivate drivers to stop to take breaks. Results underscore the need to educate and/or motivate drivers to respond sooner to warning signs of drowsiness.