In this study we examine sleep during adaptation and readaptation to different shift work schedules in the offshore oil industry. The sleep of 19 offshore workers was assessed daily for 1 week before, during the work period, and for 1 week after 3 different work schedules: (1) day (14 consecutive days of work), (2) night (14 consecutive nights of work), and (3) swing shift work (first 7 nights with night work then 7 days of day work). The workers' sleep was assessed for 84 days. Actigraphy and sleep diary estimates of sleep was applied assessing: (1) adaptation to offshore shift work, (2) sleep across the 2 offshore work weeks, and (3) readaptation after the work period. Regarding adaptation, sleep efficiency was higher when working day than night and swing shift the first week of work. Sleep quality was better during swing than regular day/night shifts the first week of work. Total sleep time was longer during day and night shift than swing shift across the 2 work weeks. Sleep efficiency, based on sleep diaries, was higher during day than night and swing shift during the 2 work weeks. There were no significant differences between the shifts in readaptation in terms of sleep. To conclude, adaptation to swing shift was more difficult than adaptation to regular day and night shifts in terms of sleep. Readaptation to day work after 1 week of night work affected sleep negatively. There were no differences between the shift schedules the week after the work period.