In a period with increasing trade and recognised potential for women’s role in business affairs, high medieval commentaries and responsa discussing yiḥud demonstrate how everyday life interacted with social concerns about maintaining the boundaries of Jewish communities, and simultaneously with legal concerns about the internal mechanics of Jewish communities. As yiḥud exposes the ways in which boundaries placed on interpersonal interactions were delineated through gendered categories, it demonstrates how everyday life interacted with the existential concerns of maintaining Jewish difference that preoccupied the writers of responsa literature. Yiḥud is an important case study in attempts to access the lived experiences of thirteenth-century Jews. By investigating sources with an eye to relationship structures, they shed light on the interaction between social, legal, institutional, and financial experiences of Jews across medieval Europe. This paper will focus on questions dealing with travel in mixed ‘caravans’ between settlements – who could travel with whom, when, and for what reasons? I will then compare these responsa and exempla with discussion of yiḥud within the Jewish settlements of Barcelona and Kehilot Shum. Were halakhic rulings regarding yiḥud more or less stringently applied outside the physical boundaries of a Jewish settlement? This paper will analyse how, through relationships governed by yiḥud, aspects of communal norms and standards were conceptualised, instantiated, and challenged at their boarders, and how these processes operated differently in different communities.