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Distinctions between Puerto Rican and Cuban cuisines are subtle in nature. Yet, the contrasting, diverging histories of these two sister islands have yielded differences in culinary representations (as seen in restaurants and cookbooks) of these cuisines in the islands and among communities abroad. Using NYC as the point of intersection, this paper utilizes cuisine as a medium to explore the divergent histories and migration trajectories of these islands. Merging field interviews with archival research, the paper explores the concept of national cuisine in a transnational framework, including representations in the islands and in NYC, differentiating insular culinary evolutions from contemporary “Nuyorican” and “Cuban-American” representations. The paper illustrates how contemporary cuisine representations mirror the migratory histories and transnational ties of these communities. While Cuban cuisine representations are tied to nostalgia and a preservation of 1950s Cuba, Puerto Rican cuisine representations aim at demonstrating current ties to the island. The analysis also reveals divergences in culinary evolutions between the islands and the communities abroad. The comparative approach focused on these two contrasting communities allows for a greater understanding of the preservation and (re)inventions of food practices using transnationalism as a framework. It bridges food, nutrition and migration scholarship, uncovering the intrinsic value of these traditional diets beyond nourishment, to their fundamental value for heritage and emotional wellbeing.