Around 20 cyclists from India embarked on long and arduous intercontinental journeys between 1923 and 1942 individually or in groups. Many of these ‘globe cyclists’, as they were often referred to by the Indian press, later wrote media articles and longer travelogues about their expeditions. This article examines the narratives of these long-distance cycling expeditions to argue that these journeys can illuminate new histories of the bicycle’s socio-cultural impact beyond the West, the self-fashioning of Indian cyclotourists as an example of complicit masculinity, and world tours as a novel form of anti-imperial counter-mobility. It does so by drawing on several historiographical subfields that have hitherto rarely been mobilized together, namely the histories of sports, masculinity, colonialism and decolonization, tourism, and (everyday) technology. The article focuses pars pro toto on the tours of Adi Hakim, Jal Bapasola, and Rustom Bhumgara (1923-1928) and Ramnath Biswas (1931-1940) that were strongly over-determined by the contexts of colonialism, anti-colonialism, and decolonisation, while nationalist masculinity represented another recurring trope.