Caribbean Martins (Progne dominicensis) are common breeders on most Caribbean islands, where they regularly roost and nest in urban areas from February through August. However, from September through January, the basic ecology of this species—its migration and wintering locations—are largely unknown. In 2012, we deployed seven geolocators and, in 2014, recovered one geolocator from a female Caribbean Martin on the Commonwealth of Dominica, a small eastern Caribbean island. Her wintering location was the western portion of the State of Bahia, Brazil, approximately 3550 km southeast of Dominica. Although the non-breeding grounds changed minimally, the fall departure date, migration route and length of migration to western Bahia, Brazil, was different between years. In October 2012, the female followed a coastal migration route along the Atlantic coast of South America, then flew south to the non-breeding grounds. However, in Oct 2013, she flew south from Dominica through Guyana, spent a few days in the Amazon rain forest, and then migrated southeast to the non-breeding grounds. These results provide insight into the repeatability of migration routes and wintering locations by this species, and serves as a first step in better understanding the Caribbean Martin’s full life-cycle.