Besides attempting a fresh look at famous debates on philosophical solitude seen through the lens of cultural labelling strategies, the tradition of retirement poetry and the travel-inspired writings of two minor Enlightenment figures, this chapter offers some reflections on the ambivalence with which early modern European intellectuals conceptualized and experienced solitude: as an empty vacuum on the verge of a divine filling, as a pathology, as a stage of civilization, as temporary respite from the cares of life or as the prelude to penetrating social critique. In so doing, solitude was something that they at once yearned for and suffered from, prescribed and condemned, celebrated and feared.