Study abroad (SA) is often equated to cultural learning, which is problematic when culture is presented as a fixed concept free of context. To challenge cultural labeling and develop students' critical consciousness, this study implemented an arts-based inquiry intervention within a United States (US) SA program in Italy. Using a Deweyan experiential frame it incorporated arts-based pedagogy, which refers to the artistic tools and strategies used to support and stimulate students' reflective learning. This qualitative case study describes the process of 13 undergraduate US students' participation in a multi-phase inquiry project as a scaffold for educators and illuminates the complexity of learning through participants' art and reflections. Findings suggest the inclusion of arts-based inquiry can support the development of critical consciousness of "cultural hybridity" and can decenter students' assumptions and perspectives to feature the voices of those around them. Additionally, the article highlights that the learning process is both complex and continual. It indicates that scholar practitioners must be aware of the potential for essentialization through representation, and therefore the need to continue to address cultural stereotypes while also guiding students to examine their own understandings of self and culture. The paper concludes with recommendations for continued improvement and implications for both the international field of SA and for educators in general who seek to expand critical thinking and meaning-making in the classroom.