The maritime historian Alston Kennerley recently noted that are few histories of seamen's mission and those that exist were written by practising pastors. Kennerley rightly observes that these histories are not ‘tempered sufficiently by discussions of the wider historical social context' and ‘awkward negative issues' such as the self-interest of the clergy themselves.[i] This paper will redress this historiographical vacuum through exploring how urban missionaries began to construct an imagined map of sailortown that would shock the bourgeoisie and justify their exploration of a heathen underworld. Moreover, in location and construction of their missionary buildings, and the development of social welfare programmes for sailors, the religious missionaries undoubtedly took their cue from their counterparts in the wider empire. The paper will focus on Portsmouth, the principal naval port in Britain during the nineteenth century. During this period, the Royal naval port of Portsmouth was a heavily fortified section of the urban coast cut adrift from the civic hub of the town, increasing its sense of ‘Otherness'. It was here that naval sailors and locals lived, worked and socialised beyond the reach and influence of the centres of civic leadership that were based in the heart of Portsmouth's civic centre. By the 1890s, the harbour's edge had become known as ‘The Devil's Acre', with its high density of public houses and brothels. This paper will explore the clergy's engagement with sailors, their motivations that underpinned the missions and their rather uneasy relationship with civic elites between 1870 and1914. Like their missionary counterparts in the outposts of the British Empire, Sailor Missionaries fashioned a homosocial society that was free from bourgeois domesticity. Gaining approval for its religious objectives, the missions afforded philanthropists the opportunity for excitement and forge relationships with sailors who were on the margins of respectability.