The recent surge of scholarship in the field of Mediterranean Studies has directed new attention to regions once considered marginal to Medieval Studies and called into question long-standing assumptions regarding the evolution of European culture and society, the primacy of northern European lands in this process, and paradigms such as the nation. These new understandings of broad historical narratives provide some of the most important developments in Medieval Studies in recent decades. This two-session workshop examines connections between northern Europe and the Mediterranean with the aim of illuminating the networks, personal ties, and cultural flows between these two regions in the Medieval period. The second session of the workshop explores the kinds of networks that helped facilitate cultural interchange and also shows how a comparative approach can undermine problematic theories about the differences between northern European and Mediterranean cultures. The first paper uses the Montfort family as a case study of a transregional aristocratic family. Though this northern French family is most famous for its involvement in the Albigensian Crusade and English politics of the thirteenth century, one branch of the family was established in Frankish Syria and Cyprus and had marriage ties to Cilician Armenia. The second paper explores how the strong links between the Valois Dukes of Burgundy and the Crown of Castile created deep cultural, artistic, and religious ties between the two regions as well as with Flanders, a flourishing region under Burgundian ducal rule. The third paper turns to a very different social level and uses an archival study to show that large numbers singlewomen, including enslaved women, were active in the economic and social life of a variety of Mediterranean ports. The paper then uses these findings to undermine an influential theory that a pattern of late marriage in northern Europe separated it from Mediterranean regions and contributed to its supposed advancement over the “backward” south. The first two papers reveal how deeply intertwined the elites of northern Europe and the Catholic Mediterranean were and help explain why cultural influences could flow so freely. The third paper illustrates how a more intense study of Mediterranean regions can correct problematic ideas about distinctions between northern and southern Europe.