Sleep–wake cycle disruption and seasonal variation in mood and behavior have been associated with mood disorders. This study aimed to investigate the lifetime characteristics of the sleep–wake cycle and its association with the lifetime characteristics of seasonality in individuals with bipolar disorder. Circadian preference, regularity of bed–rise time, and seasonality were evaluated on a lifetime basis using the Composite Scale of Morningness, the Sleep Timing Questionnaire, and the Seasonal Pattern Assessment Questionnaire in clinically stable individuals with bipolar I/II disorders (n = 103/97) and healthy controls (n = 270). Bipolar groups were more likely to have evening preference and irregular bed–rise time. These characteristics were interrelated and, particularly, more prevalent in bipolar II disorder. Seasonality, which was also more prevalent in the bipolar groups, was associated with evening preference and irregularity of the weekday bed–rise time.