In this public conversation, Brian Russell Roberts and Michelle Ann Stephens talk about their work in the field of Archipelagic American Studies and about the intersections of this field with Mobility Studies. They discuss archipelagic thinking, islands and the insular, the borderwaters, alternative mapping, and the ways in which thinking with the archipelago foregrounds relational entanglements and mobilities. The conversation was part of the workshop “Archipelagic Imperial Spaces and Mobilities” that took place in Leipzig in July 2021.