Reports of humpback whale (Megaptera novaeangliae) song chorusing occurring outside the breeding grounds are becoming more common, but song structure and underwater behavior of individual singers on feeding grounds and migration routes remain unknown. Here, ten humpback whales in the Western Antarctic Peninsula were tagged in May 2010 with non-invasive, suction-cup attached tags to study foraging ecology and acoustic behavior. Background song was identified on all ten records, but additionally, acoustic records of two whales showed intense and continuous singing, with a level of organization and structure approaching that of typical breeding ground song. The songs, produced either by the tagged animals or close associates, shared phrase types and theme structure with one another, and some song bouts lasted close to an hour. Dive behavior of tagged animals during the time of sound production showed song occurring during periods of active diving, sometimes to depths greater than 100 m. One tag record also contained song in the presence of feeding lunges identified from the behavioral sensors, indicating that mating displays occur in areas worthy of foraging. These data show behavioral flexibility as the humpbacks manage competing needs to continue to feed and to prepare for the breeding season during late fall. This may also signify an ability to engage in breeding activities outside of the traditional, warm water breeding ground locations.