Tolstoi was well acquainted with the phenomenon of “holy wanderer” or “strannik”: His estate Iasnaia Poliana was located close to the main road to Kyiv where each summer scores of pilgrims passed by. However, in the Russian strannik concept, the focus is not – as for the pilgrim – primarily on reaching a sacred site, but on the journey, on being underway. Wandering becomes a goal in its own right. This kind of spirituality appealed to Tolstoi and during one of his visits to Optina Pustyn he consciously emulated it: He set off on foot, wearing a peasant jacket, bast shoes tied with rags, knapsacks on his back, and with a wanderer’s staff in the hand. It would be misleading to say that Tolstoi simply took over a “form” and filled it with his own content. He was also concerned with and fascinated by the “content side” of holy wandering – the restless, seeking attitude that spurns the security of house and hearth and trusts that God will provide guidance where to go. But to Tolstoi, the inner journey was just as important as the physical. Between “Tolstoi the holy wanderer” and the age-old Orthodox wanderer tradition there is both rupture and continuity.