Antarctica’s extreme environment poses unique challenges for the people who occupy its isolated and confined scientific sites in the austral winter. Understanding how individuals and teams adapt under these difficult circumstances, and the factors that influence their wellbeing, is vital not only to improving the experience of Antarctic over-wintering staff, but also to understanding how best to operate in other Isolated, Confined and Extreme (ICE) environments, including long-term space travel. This paper offers a dual case study of the Amundsen-Scott South Pole Station (US) and Halley Research Station (UK), using a multi-disciplinary approach to identify and investigate the complex, nuanced factors influencing wellbeing and adaptation for Antarctic winterers. Factors related to the social relationships, attitudes to work, and the physical environment are illuminated using original interviews and archival research. This paper also argues for the necessity of multi-disciplinary collaboration in adaptation research. The combination of psychological analysis and qualitative historical geographical research presented in this paper, as well as the opportunities for multi-site comparison offered by taking a collaborative approach, enable greater insights to be drawn from both of the individual studies presented here. By presenting the challenges and dynamics of life in these stations in great detail, this paper contributes to research on wellbeing and adaptation in ICE environments, as well as Antarctic humanities and social sciences scholarship focused on living and working in Antarctica.