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A less-than-fortunate failing relationship, pending unemployment, fear of enlistment in the army, and sinus issues brought Leonard Bernstein to Key West in late August of 1941 for a 10-day vacation that changed the trajectory of his compositional career. While Bernstein’s successes with his “Clarinet Sonata for Piano,” Fancy Free, On the Town, and West Side Story are tied to his positionality in New England, the sunny and sailor-filled paradise of Key West, Florida, also played a monumental role in Bernstein’s early career. During his visit, Bernstein started his clarinet sonata and an unfinished ballet titled Conch Town (1941)—a composition that contains the musical framework for the iconic “America” from West Side Story premiered 16 years later in 1957. Through the live music and radio influences he likely experienced in Key West, Bernstein was able to gain exposure to Afro-Latin styles of music that inspired Cuban compositional styles in his earliest and highly successful compositions. Furthermore, Bernstein was exposed to swaths of sailors during Key West’s boom in population due to increasing tensions surrounding WWII. Sailors later served a role in Bernstein’s queer fantasies as seen in his ballet Fancy Free and musical On the Town. This paper thus examines both the sociocultural and musical landscape of Key West during Bernstein’s initial visit to the island to contextualize the importance of this short vacation to his personal and professional life. Through using resources from the Works Progress Administration of Florida, letters to and from Bernstein, biographical information about Bernstein and his early compositions, and histories of Key West and Cuban music, I curate a pastiche of sources to provide a narrative of the vibrant musical life of Key West in and around 1941 and its subsequent impact on Bernstein’s compositions. By examining Bernstein through the lens of Key West’s music scene as a place for cultural and historical exploration, I show the power of decentering composers from the places they are most known for. Doing so, I hope to further develop scholarship on the connections between musical ecology of place and composers toward a more globalized perspective.