Migratory birds often have tightly scheduled annual cycles, in which a delay in one event can have carry-over effects on the timing of later events, which may ultimately impact reproductive output. We utilize a large-scale study system to investigate carry-over effects in timing: the variation in annual schedules of individual Arctic Skuas Stercorarius parasiticus at 12 breeding sites between East Greenland and West Siberia in relation to their use of seven widely divergent wintering areas across the Atlantic Ocean, Mediterranean Sea and Indian Ocean. We studied whether migration schedules differ among breeding populations as a function of their choice of wintering areas, and predicted that migrations over larger distances, with tighter schedules, would provide less room for compensating delays. Breeding at higher latitudes led not only to later timing of reproduction and migration, but also to different allocation of time to different phases, with faster spring migration and shorter time between return to the breeding area and clutch initiation. In contrast, breeding latitude had no effect on the duration of autumn migration and wintering period. Wintering area was consistent within individuals among years and had an additive effect on annual schedules, with more distant areas associated with more time spent on migration and less time spent in the wintering areas. Tracked skuas were able to adjust the period spent in the non-breeding area, regardless of the distance from the colony, which generally buffered the variation in timing of autumn migration. Despite individual variation in migration distances of thousands of km, skuas from the same population arrived largely synchronously at their breeding area. The lack of a consistent effect of migration distance on timing of return to the breeding grounds indicates that individuals synchronize their arrival with others in their population despite extensive individual differences in migration strategies.