Henry Robinson’s writings and pamphlets offer a rare mix of works by a London merchant interested in tolerance, trade, economy, social reforms, law, education and politics. Published between the 1640s and the early 1650s, his texts were deeply rooted in the most innovative thought of his time, dialoguing with Bacon, Selden, Mun, Hartlib, Milton, and Galilei. An active merchant, he was charged with important responsibilities during the period of the Commonwealth and Protectorate. This essay focuses on a neglected aspect of Robinson’s life and career, namely his stay in the Tuscan port city of Livorno in the early 1630s. It looks to demonstrate that Robinson’s economic and religious thought bore the imprint of his Italian experience and of the complex social, political and religious context of the Mediterranean in the early seventeenth century. Through a close-reading of a selection of his numerous tracts and of archival material found in Tuscan archives, this article argues that Robinson’s experience and knowledge of the Mediterranean context played an important role in his original conceptions of tolerance and his new ideas on social and economic matters. More broadly, the case of Robinson highlights the intense economic, political and intellectual connections between Tuscany and England in the first half of the seventeenth century.