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The paper demonstrates a microhistory approach to the development of cruising as a form of leisure in the early twentieth century of American history. Using the 1934 Morro Castle disaster and the subsequent attention the ship and its survivors received, this paper provides a window into an unexplored topic of American leisure. This paper is unique in its finding because the disaster provided numerous firsthand accounts of cruising in the 1930s. The findings illustrate that this form of leisure was directly connected to larger events and trends of the time, including the Great Depression, Prohibition, and America’s Cuban connection. Cruising as a form of leisure, thus, developed out of a social and cultural demand, illustrating escapism in a tumultuous period.