Calle de la Fortaleza in Old San Juan, Puerto Rico, has a complex history that reflects the island’s colonial past and ongoing struggles for self-determination. This project aims to investigate the implications of colonization on the built environment and its impact on contemporary society, focusing on the popular tourist site of Calle de la Fortaleza in Old San Juan. Old San Juan is made up of colonial-style buildings that reflect the architectural style of their period, including the Governor’s Mansion, a renaissance style building and a historical site for protests against political corruption. The project aims to understand the impact of colonization on the built environment and its ongoing legacy in contemporary society while shedding light on the intersection of colonial history, architecture, and activism, and to demonstrate how the built environment can be used as a site of resistance and protest against social and political injustices. Finally, the project will consider the future of Calle de la Fortaleza as a site for political activism and resistance through new architectures and programs for healing that better represent the mixed heritage history of Taino peoples, the original Pre-Columbian inhabitants.