This paper sets out to interrogate the reality of secondary schooling in one part of the Caribbean, through a case study exploration of the "gender regimes" of four secondary schools in the small Eastern Caribbean nation state of Antigua and Barbuda. In Antigua, as in the Caribbean region more broadly, the focus of attention has been on boys due to their apparent underachievement. However, this qualitative research project found highly complex gender dynamics. Inside classrooms, teachers' gendered assumptions lead boys to receive more positive and negative attention, leading both girls and boys to be disadvantaged in different ways. Outside the classroom, many "hidden" gender inequalities were found to exist, inasmuch as these were not identified in teachers' narratives and in discourses concerning policy; such "hidden" inequalities included the pressure both girls and boys are under to perform gender along normative lines and girls' experiences of sexual harassment from boys.