This dissertation explores the social and cultural worlds of free people of color in the African Americas. It investigates how free people of color navigated social life and negotiated the boundaries of racial difference in two crucial mainland American port cities: Cartagena, along the Caribbean coast of Colombia, and Charleston, situated in the heart of the South Carolina lowcountry in the United States South. Transnational and comparative in perspective, this work reveals how free people of color leveraged laws, institutions, personal reputations, and carefully cultivated social networks to improve their individual circumstances as well as those of their families and communities. This dissertation reveals the complex parallels and differences between the challenges and opportunities for free people of color in the urban Americas, particularly in their efforts to achieve social and economic mobility. It argues that even when their means to achieve social distinction differed, efforts by free people of color to improve their individual circumstances challenged the logic of white racial ideologies and subtly questioned the legitimacy of American racial hierarchies. While free people of color often declined to confront more directly the systems of white supremacy that undergirded American society, the work of free people of color to achieve social and economic uplift paved the way for the continued struggle to achieve respectability, freedom, citizenship, and equality.