The aim of this study was to determine the relationship between circadian preferences, regularity of sleep patterns, sleep problems, daytime sleepiness and daytime behaviour. As a part of an epidemiological survey on sleep in a representative sample of Italian high-school students, a total of 6631 adolescents, aged 14.1-18.6 years, completed the School Sleep Habits Survey, a comprehensive questionnaire including items regarding sleep, sleepiness, substance use, anxiety and depressed mood, use of sleeping pills, school attendance and a morningness/eveningness scale. The sample consisted of 742 evening-types (315 males and 427 females; mean age 17.1 years) and 1005 morning-types (451 males and 554 females; mean age 16.8 years). No significant sex differences were found for morningness/eveningness score. Eveningness was associated with later bedtime and wake-up time, especially on weekends, shorter time in bed during the week, longer weekend time in bed, irregular sleep-wake schedule, subjective poor sleep. Moreover, evening types used to nap more frequently during school days, complained of daytime sleepiness, referred more attention problems, poor school achievement, more injuries and were more emotionally upset than the other chronotype. They referred also greater caffeine-containing beverages and substances to promote sleep consumption. Our results suggest that circadian preference might be related not only to sleep pattern, but also to other adolescent behaviours.