This chapter investigates the travels of Cassandra Grimaldo (c. 1540–1618), a member of the renowned Grimaldo family of Genoese financiers, as she crossed the Mediterranean from Genoa to Castile and other Spanish cities where her husband had considerable land investments. The daughter of Nicolao Grimaldo, banker to the Spanish Habsburgs, Cassandra married her father’s business partner, Esteban Lomelín, another Genoese financier whose financial transactions were based in Granada and Madrid, among other cities. The considerable difference in their ages, and the fact that she had no children, allowed her to take over her husband’s business. On his death, she assumed the reins of an international financial enterprise at the time that the Spanish Monarchy consolidated power in Europe.