This chapter introduces locales that formed part of the turtlemen's mobile and transnational world. It explores the interconnectedness between the Cayman Islands and various circum-Caribbean communities in Honduras, Costa Rica, Nicaragua, Cuba, and Colombia through ethnographical accounts, missionary reports, oral history accounts, and newspaper reports. It also focuses on the way a seafaring culture of Caymanians led to temporary and permanent migration, the formation of transnational as well as transcultural families, and the transmittal of maritime and cultural knowledge among turtlemen of multiple nationalities. The chapter argues that the Caymanian seafaring culture, particularly, turtle fishing, facilitated the creation and recreation of a dynamic contact zone of ongoing transnational and occasional cross-racial encounters among indigenous, white, and Afro-Caribbean inhabitants.