Barry Island was one of the most cherished leisure spaces in twentieth-century south Wales, a playground for generations of working-class day-trippers. This book considers its rise as a seaside resort and reveals a history that is much more complex, lengthy, and important than has previously been recognized. As conventionally told, the story of the island as tourist resort begins in the 1890s, when the railway arrived in Barry. Yet Barry had been functioning as a watering hole since the 1790s—yet decades of tourism produced no sweeping changes. Barry remained a district of “bathing villages” and hamlets, rather than developing into an urban resort, as might have been expected. As such, the history of Barry Island challenges us to rethink the category of “seaside resort” and forces us reevaluate Wales’s contribution to British coastal tourism in the long nineteenth century. It also underlines the importance of the agency of those who visited the island. Powerful landowners shaped much of the island’s development, but ultimately it was the working-class visitors who turned it into south Wales’s most beloved tripper resort.