Imagining the Tropics is a history of the development of tourism in the Caribbean from the 1910s through the 1970s that focuses on the ways women’s labors of hospitality, writing, and advocacy built the industry and its ubiquitous imagery of tropical island relaxation, escape, and romance. By examining a range of sources, engaging a wide array of women protagonists, and looking broadly across multiple Caribbean island-states including Jamaica, Cuba, the Bahamas, Barbados, the Dominican Republic, Haiti, Puerto Rico, Trinidad and Tobago, and the US and British Virgin Islands, it seeks to understand how the region came to be sold as a romantic escape from the “troubles” of the modern world. By putting women at the center of Caribbean tourism history—as both its ambassadors and objects of desire—it seeks to explain some of the complicated contradictions that plague the business of pleasure but also to point toward ways of building alternative models to its present and past extractive realities.