This dissertation considers the Grand Duchy of Tuscany's long-distance activities during the reigns of Grand Dukes Francesco I (r. 1574-1587) and Ferdinando I (r. 1587-1609), including long-distance commercial and imperial projects, military adventures, diplomacy and espionage, collecting, and information-gathering, to explore how the vast empires and emergent global economy of the late sixteenth and early seventeenth century functioned in practice, the role of small powers in these systems, and the wide range of prospects contemporaries saw. The projects and adventures of Tuscan affiliated diplomats, spies, mariners, and merchants who traveled to Morocco, Syria, Iran, Muscovy, India, China, Japan, Spanish America and Brazil reveal an early modern world still very much in flux, open to an almost limitless array of possibilities. This case study of Tuscany's role demonstrates both the breadth of Tuscan ambition and the centrality of politics to structuring participation in the global economy and overseas empire in the early modern world, which in turn suggests a need to revise traditional nationalist and determinist accounts of Europe's engagement with the broader world.