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This comparative study investigates the socio-legal and institutional conditions of the settlement and residence of Jews in several Mediterranean port cities during the early modern period. Focusing first on the Tuscan port of Livorno, it analyzes the nature and content of the privileges granted to Jewish merchants and former crypto-Jews at the end of the sixteenth century. It retraces the political and economic justifications throughout the history of their negotiation, based on reasons of state and the assertion of the prince’s sovereignty, which legitimized the acceptance of Sephardim in Livorno. Second, the Tuscan edicts of the 1590s are linked to the “philosemitic mercantilism” of the sixteenth century, and to the competition of the Mediterranean port cities, from Nice/Villefranche to Ancona and from Venice to Livorno. The uncertainty of the rules favoring Jews is highlighted here, as well as the presupposed link between economic growth and the invitation of Jews to settle and trade in port cities. However, the indecisive policies here are a good indicator of the unstable institutional environment of these places. Lastly, a third section is devoted to the competition of “free ports,” by comparing the fluctuating conditions of the settlement of Jews in Nice/Villefranche, Genoa, and Marseille in the seventeenth century. This comparison shows that the Jewish presence, subject to numerous political changes, was less a vital ingredient of the “free port” than an effective revealer of its institutional environment, which was relatively favorable and open to foreign traders.