This chapter studies the connections that allowed Cunas and Wayuu to develop a lifestyle or worldview that can be called a cosmopolitan, Greater Caribbean way of being in the world. It also emphasizes how the interactions associated with cosmopolitanism put these indigenous groups on an equal footing with European allies and rivals and allowed them to successfully sustain their challenge to Spanish authorities. By emphasizing indigenous mobility, multilingualism, technological capacity, and political autonomy, the chapter challenges cartographic fictions of territorial control embedded in European-drawn maps of the Caribbean and sheds light on European perceptions of indigenous peoples. In short, this chapter argues that the Cunas and the Wayuu, like the people Ira Berlin and Jane Landers called Atlantic creoles, were cosmopolitan in the fullest of senses. The chapter is organized in three sections. The first one looks at the geographic spaces inhabited by Cunas and Wayuu. Drawing on Spanish maps prepared as part of military campaigns that sought to conquer maritime Indians, this section uses Spanish cartographic narratives to tell the story of maritime Indians’ political autonomy and Spanish veiled recognition of that autonomy. The second section analyzes the traits that made maritime Indians cosmopolitan and the ways in which cosmopolitanism allowed them to successfully assert their political independence in the face of constant Spanish attempts to conquer them. The last section contrasts the ways in which maritime Indians envisioned themselves as actors in the transimperial Greater Caribbean with how Spanish authorities saw them.