Puerto Rico and Cuba, linked by a common colonial history, culture, and tropical environments, have similar cuisines. The islands’ shared historical trajectories have been increasingly divergent in the last century, especially since the 1959 Cuban Revolution. This paper analyzes the concurrent social changes since the 1950s in these two contexts, through the work of two iconic cookbook writers, Carmen Valldejuli (Puerto Rico) and Nitza Villapol (Cuba). Writing and publishing during the second half of the twentieth century, these women’s books became an important part of the culinary imagination in their respective islands and diaspora communities. This article analyzes how their work reflects their personal stories and changing social contexts by comparing the earliest and latest editions of their books. Differences between Puerto Rican and Cuban cuisines, as portrayed in the cookbooks, are assessed and contextualized in their respective sociopolitical contexts. This analysis of the production and transmission of culinary traditions offers a novel insight on local and transnational manifestations of these islands’ sociopolitical transformations during these decades.