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This article investigates the start of Florence’s approach to Ottoman Constantinople. It analyses the elements that enticed the Florentine Signoria to reconsider its commercial interest in Constantinople by highlighting the political role of the Ottoman sultan. In addition, this study intends to shed light on the difficulties the Florentine establishment faced in its diplomatic effort to successfully establish a profitable state trade route with the former Byzantine capital. The Signoria’s diplomatic groundwork has never been extensively studied, but doing so reveals how an apparently routine matter of administration, the negotiations over the safe-conduct with the Kingdom of Naples, became a salient political issue that took nearly three years (1455–1458) to resolve. The article also aims to make an original contribution to the history of the Florentine Mediterranean thanks to material from previously unconsulted sources.

A Dwarf Among Giants: A Diplomatic and Political Reading of Florence’s First Commercial Expedition to Ottoman Constantinople