More than 6 million Britons travelled to southern Africa during the Second World War as evacuees, to convalesce, for military training and en route to the battle fronts of Asia, the Pacific, and the Middle East. Wartime travel provided more Britons than ever before with first-hand experience of white privilege and the lifestyle it provided in the settler colonial societies of southern Africa, convincing many to relocate there permanently. Wartime memoirs and letters reveal the ways in which the war both led to the strengthening of existing personal relationships between the UK and the settler colonies of southern Africa and the formation of new ones, including marriages. They also suggest that, for many, the heightened experience of the war and the exhilaration of living through extraordinary times made the return to normal life in Britain difficult. Southern Africa, with its combination of the familiar and the exotic, was an appealing alternative. Though the vast majority returned to the UK after the war, this collective first-hand experience influenced broader perceptions of South Africa and Southern Rhodesia as places of abundance, hospitality, and opportunity. This case study draws attention to the way the wartime travel provided more Britons than ever before with direct experience of imperial sites and suggests that this contributed to the continuing significance of empire, and especially the Dominions in post-war Britain.