Migratory birds spend periods of the year in different locations as a response to seasonal changes in environmental suitability. They are classified as either ‘niche-trackers’ or ‘niche-switchers’, depending on whether they track or switch environmental conditions throughout the year. However, the relationship between these strategies and their migratory behaviour is still unclear. Here we examine whether migratory European Robins Erithacus rubecula and Eurasian Blackcaps Sylvia atricapilla track environmental conditions between breeding and wintering areas and whether their behaviour differs from that of their sedentary counterparts. We used ringing data for both migratory and sedentary individuals wintering sympatrically in the Iberian Peninsula to assess the environmental conditions relating to their seasonal distributions. We explored seasonal niche-tracking using two multivariate analyses with alternative sets of predictor variables (landscape and climate) to generate different environmental scenarios. Our results show that migratory individuals track similar climatic conditions throughout their seasonal distributions, whereas sedentary birds cope with great variation in climate over the course of the year. In addition, migratory birds show less seasonal overlap in the landscape structure of their chosen habitats compared with sedentary individuals. These results suggest that there is a trade-off between, on the one hand, the cost for migrants of travelling long distances and, on the other, the increased flexibility required by sedentary birds if they are to tolerate a wider suite of environmental conditions within their permanent ranges. Given that sedentary populations in the southern Iberian Peninsula seem to be linked to populations of migratory individuals of these two species that started to move northwards after the last glacial cycle, the observed patterns suggest that migrant birds represent a fraction of the southern population that is specialized in the exploitation of a narrower range of environmental conditions.