This introduction lays out the major themes and parameters of the book. It delineates the multi-textured meanings of “fairyland”—a term crafted by white urban boosters by the early twentieth century—to a diverse group of people who traveled to and settled in the Greater Miami area from 1890 to 1940. The introduction stresses how migration and immigration, tourism, and trade to and from the Caribbean proved central to shaping the image of Miami as fairyland, a moniker that allowed gender and sexual transgressives to carve out a space for themselves in the nascent city. It emphasizes the significance of Miami’s queer past by situating this research in the existing literature, particularly in the fields of queer, transnational, Caribbean, tourism, and immigration and migration history. This introduction also offers an overview of each chapter and the book’s research methods, methodology, and use of archives.