Aim: Knowledge of broad-scale biogeographical patterns of animal migration is important for understanding ecological drivers of migratory behaviours. Here, we present a flyway-scale assessment of the spatial structure and seasonal dynamics of the Afro-Palaearctic bird migration system and explore how phenology of the environment guides long-distance migration. Location: Europe and Africa. Time period: 2009–2017. Major taxa studied: Birds. Methods: We compiled an individual-based dataset comprising 23 passerine and near-passerine species of 55 European breeding populations, in which a total of 564 individuals were tracked during migration between Europe and sub-Saharan Africa. In addition, we used remotely sensed primary productivity data (the normalized difference vegetation index) to estimate the timing of vegetation green-up in spring and senescence in autumn across Europe. First, we described how individual breeding and non-breeding sites and the migratory flyways link geographically. Second, we examined how the timing of migration along the two major Afro-Palaearctic flyways is tuned with vegetation phenology at the breeding sites. Results: We found the longitudes of individual breeding and non-breeding sites to be related in a strongly positive manner, whereas the latitudes of breeding and non-breeding sites were related negatively. In autumn, migration commenced ahead of vegetation senescence, and the timing of migration was 5–7 days earlier along the Western flyway compared with the Eastern flyway. In spring, the time of arrival at breeding sites was c. 1.5 days later for each degree northwards and 6–7 days later along the Eastern compared with the Western flyway, reflecting the later spring green-up at higher latitudes and more eastern longitudes. Main conclusions: Migration of the Afro-Palaearctic landbirds follows a longitudinally parallel leapfrog migration pattern, whereby migrants track vegetation green-up in spring but depart before vegetation senescence in autumn. The degree of continentality along migration routes and at the breeding sites of the birds influences the timing of migration on a broad scale.