This chapter illustrates how parents and their young adult children approached making decisions about how they would walk the Camino de Santiago together and the role that Camino guidebooks, published pilgrims’ narratives, and online sites played in their expectations and design. Drawing largely from formal interviews with pilgrims, it highlights the abundance of choices these parents and young adult children faced regarding hospitality, travel, and digital technologies. The chapter emphasizes how, through familiar mechanisms and processes of buying family leisure time, they pursued the Camino’s call to be open to the unknown and its promise of sacred connection to others, nature, and mystical encounters.