Using a transnational framework, this paper focuses on four graduates of Gipsy Hill Training College (GHTC) for nursery school teachers in London, United Kingdom, in the early to mid-twentieth century. Firstly, I explore GHTC's progressive ideals and highlight ways in which its principal, Lillian de Lissa, encouraged students to "think internationally". She was especially proud that a handful of students from countries such as China, Turkey and Canada studied at Gipsy Hill. These included Nevin Nouri and Bek Keng Chui, whose experiences are explored in the second section of the paper. Likewise, British graduates "who carried Gipsy Hill to the ends of the earth" featured prominently in the college magazine, the Gipsy Trail. Finally, I examine reports from Marjorie Sanders and Barbara Boal for the ways in which they represented their lives and work overseas to readers of the Gipsy Trail. Together, de Lissa and GHTC graduates constructed the college as a progressive educational institution whose influence transcended national boundaries. However, they exposed a range of social divisions in their portrayals of people and places "in the uttermost parts of the earth" in the process of articulating their ideals.