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Building on over two decades of ethnographic and archival research, this project explores the influence of two linked African Diaspora artist retreats (1995-2015) that shaped the creative trajectories of a generation of African American and Afro-Latin artists. Located in Portobelo, Panama, these retreats allowed artists to foster bonds of kindship and community while engaging with transnational Black aesthetics, cultural politics, and performance. Central to this study is Taller Portobelo, an artist cooperative founded in the early 1990s by Prof. Arturo Lindsay, photographer Sandra Eleta, and visual artist Yaneca Esquina. It became a key site for African-descended artists to collaborate, share knowledge, and build community. This vision expanded to include the Spelman College Portobelo Summer Artist Retreat and Creative Currents Arts Collective, which created opportunities for deeper connections between U.S. and Panamanian artists. Through archival research, oral histories, and ethnographic methods, I examine how these retreats reshaped artists’ perspectives and contributed to broader cultural movements in the African Diaspora. The project’s significance lies in its focus on the intersection of art, activism, and community-building, contributing to fields like African Diaspora studies, Latin American studies, and performance studies. Its interdisciplinary and transnational approach addresses a gap in scholarship by highlighting the cultural exchanges between U.S. and Afro-Latin artists. By integrating digital humanities tools, this work enhances accessibility and provides a multi-modal understanding of the rich cultural legacy of these artist communities.