This article researches the ways in which seamen sailing to the Mediterranean on Dutch mercantile vessels during the seventeenth century exercised several forms of economic agency. Fully congruent with the entrepreneurial spirit of the Dutch Golden Age, seamen made an active effort to improve the socioeconomic position of their households, transcending the narrow categorization of them as exploited maritime workers. They made use of three forms of economic betterment. First, seafarers shipped their own merchandise, which they traded abroad or at home. The major role of seamen’s wives in domestic markets made the small-scale entrepreneurship of sailors a family affair. Second, mercantile ships could engage in maritime warfare. Letters of commission allowed skippers to attack enemy vessels, with the spoils divided among the crew. This option was regularly taken by Mediterranean-bound ships, which were more heavily armed. Third, several skippers, officers, and ordinary seamen opted for a life of corsairing. Forced through the threat of slavery, or out of their own free will, seamen could choose to become renegades and embark on, or even command, ships from the North African regencies. These options were most prominently available to crews setting out to the Mediterranean, with its dense commercial networks and its high presence of vessels sailing under the different flags of European nations, the Ottoman Empire, or the North African city states. The old Middle Sea provides, thus, the perfect testing ground to analyze the economic agency that seamen possessed during the early modern period.