The thesis traces the persistent anachronistic characterisation of Anglo-Florentines in the twentieth century, reassessing the relationship of these individuals with the cultural heritage and socio-physical reality of the city. The title of the thesis has been formed in opposition to the post-war mythologisation of a golden ring of Anglo-Florentines, a distinctly disconnected and highly privileged community. This thesis reconsiders the boundedness of Anglo-Florence by drawing behavioural comparisons between Britons in Florence with other those at other sites of colonisation and settlement, and by placing emphasis upon the varying and contested practices of its supposed members. Moreover, through a combination of methodological approaches, including spatial mapping and Social Network Analysis, this study unpacks the physical and cultural presence of Britons in the city, whilst also proposing a more concrete visualisation of prominent Anglo-Florentine actors, defined by their potential for transnational social agency. The thesis carries forward this revised understanding of Anglo-Florentine actors into the context of the First World War as a period in which anxieties over Britain’s insecurity saw Foreign Office officials consider engagement with new modes of propaganda and diplomacy. As a “pernicious spot” for pro-German sentiment, Florence’s British residents were mobilised as key facilitators and mediators of engagement and exchange with Italian counterparts, supported and financed by the British Government. This thesis concludes by exploring the confluence of these local social and broader political pressures through the establishment of the British Institute of Florence. It is shown how polarised opinion over the operation of the institute, and to whom it should cater, ultimately aided in the establishment of a more innovative and robust institution, one which would consequently serve to present and preserve the idea of Anglo-Florence’s homogeneity and its historic cultural significance across the city.