The sky is an aerial space of circulation; it can be understood as a medium, defined as a vehicle that carries meaning. If we dig a little bit deeper into the idea that the sky is a medium or a milieu (in an ecological sense), we can enlarge our horizons of what constitutes media. This include not only antennas, cell phones, and radio sets, but, more inclusively, natural and cultural systems that allow goods, objects, and, by extension, systems of beliefs to circulate. The sky becomes a social space of circulation and interactions that allows things, people, and animals to connect and exchange. The sky offers an “infrastructure of circulation,” like cables that allow electricity to travel, and drains let water flow. In approaching the sky as a medium in which information circulates in all directions, this book reclaims a space—formerly left for dreamers or aeronautical engineers—of critical engagement. The stories showed that aerial imagination is intertwined with the politics of place, economy, and race. The sky is a historically and culturally constructed concept that is interpreted and imagined in various ways. It is changeable and it speaks to a historical moment. Aerial Imagination in Cuba encourages readers to direct their gaze towards imagined spaces or media and to potentially reshuffle the ways in which we normally assemble the material and immaterial world we inhabit.