This paper compares the patterns of socio-spatial peri-urban change in two post-socialist state capitals: Havana, Cuba (2.1 million) and Sofia, Bulgaria (1.3 million). The comparison between patterns of post-socialist peri-urban change in Havana and Sofia is instructive because it illustrates precisely how spatial patterns reflect social changes. We first out line the global diversity in peri-urban development patterns, and contrast those in socialist and capitalist cities as described by the literature. Then, we discuss the typical pattern of post-socialist peri-urban development, also according to the literature. Third, we summarize empirical findings for the development of Sofia’s periphery since 1990. Fourth, we present the current state of Havana’s outskirts. In conclusion, we reflect upon the likelihood of Havana following Sofia’s post-socialist peri-urban model, if Cuba is to eventually enter the capitalist realm.