An important issue in migration research is how small-bodied passerines pass over vast geographical barriers; in European-African avian migration, these are represented by the Mediterranean Sea and the Sahara Desert. Eastern (passing Eastern Mediterranean), central (passing Apennine Peninsula) and western (via western Mediterranean) major migration flyways are distinguished for European migratory birds. The autumn and spring migration routes may differ (loop migration) and there could be a certain level of individual flexibility in how individuals navigate themselves during a single migration cycle. We used light-level loggers to map migration routes of barn swallows Hirundo rustica breeding in the centre of a wide putative contact zone between the north-eastern and southern-western European populations that differ in migration flyways utilised and wintering grounds. Our data documented high variation in migration patterns and wintering sites of tracked birds (n = 19 individuals) from a single breeding colony, with evidence for loop migration in all but one of the tracked swallows. In general, two migratory strategies were distinguished. In the first, birds wintering in a belt stretching from south-central to southern Africa that used an eastern route for both the spring and autumn migration, then shifted their spring migration eastwards (anti-clockwise loops, n = 12). In the second, birds used an eastern or central route to their wintering grounds in central Africa, shifting the spring migration route westward (clockwise loops, n = 7). In addition, we observed an extremely wide clockwise loop migration encompassing the entire Mediterranean, with one individual utilising both the eastern (autumn) and western (spring) migratory flyway during a single annual migration cycle. Further investigation is needed to ascertain whether clockwise migratory loops encircling the entire Mediterranean also occur other small long-distance passerine species.