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Travel philanthropy is an evolving phenomenon. It owes its origins to rising frustrations with conventional aid and traditional philanthropic giving and is seen as development assistance enabling resources to flow directly from the tourism industry into community development and conservation initiatives. Philanthropists have long sought to achieve social transformation, and travel philanthropy in all its forms has evolved through the democratization of charity, as a kind of “doing good” through “giving back” whilst travelling. This paper evaluates values, practices and impacts of traditional, modern and post-modern philanthropy. Drawing upon evidence emerging from a longitudinal study, which involved the retrospective evaluation of personal diary entries, participant observations and semi-structured interviews about the transcontinental Plymouth–Banjul (car) Challenge (PBC), it exemplifies how an initiative can evolve across all three philanthropic approaches. It further debates critical understandings of the problematic travel philanthropy concept and its role in stimulating sustainable development in sub-Saharan Africa. [ABSTRACT FROM AUTHOR]