This paper examines The History of Mary Prince as a pedagogical tool for exploring complexities within the Black Diaspora. As Paul Gilroy’s articulations of the Black Atlantic inform my approach, Prince’s circuitous journey through the West Indies and England situates her process of becoming as one mired in longing and loss. Encouraging students to consider Prince as a wandering soul in search of not only freedom, but also solid familiar connections lays the foundation for merging her narrative with other enslaved Black people traversing countries and regions on ships against their will. Ample research material available on the survivors of the 1858 illegal ship enslaving Africans “Wanderer'' offer an opportunity to consider the constructions of Black Atlantic identities in which formerly enslaved Black people forge connections with each other while longing for a return to Africa. Additionally, Tessa Mars’ and Yinka Shonibare’s art forms a bridge for conceptualizing Black diasporic identities. Because the Caribbean is often perceived as a perpetual space of fantasy and play, The History of Mary Prince also challenges misconceptions of slavery as an institution peculiar to the United States. Of her brutal slaveholder sending her to another island, Prince expresses competing emotions, “At length he put me on board the sloop, and to my great joy he sent me away to Turk’s Island. I was not permitted to see my mother or father, or poor sisters and brothers, to say goodbye, though going away to a strange land, and might never see them again.” Encouraging students to consider Prince as a wandering soul in search of not only freedom but also solid familiar connections lays the groundwork for merging Prince’s narrative with other enslaved Black people traversing countries and regions on ships against their will. Ample research material available on the survivors of the 1858 illegal ship enslaving Africans “Wanderer” serves as my teaching tool for considering the constructions of Black Atlantic identities in which formerly enslaved Black people forge connections with each other while longing for a return to Africa. One of these survivors, Cilucängy, expressed in a letter his desire to return to his homeland: “I am bound for my old home if God be with me.” My essay also draws on student reactions to Yinka Shonibare’s art piece entitled “Wanderer.” Shonibare’s artwork forms the bridge for conceptualizing the more complex definitions of the Black Atlantic, Black Diaspora, and transnational identities.