I did meet a young French man when I was in Italy who was on a providence pilgrimage on his bike, cycling about 150km a day with no plans of where to stay, he would show up in a village or town and just begin knocking on doors and asking people if he could stay the night. He told me he always got a place and was even offered a meal many times, and his hosts were often delighted to have his company.
The story inspired me, but I'm still not brave enough to try it myself. The idea is to trust completely on the providence of God in the form of your fellow man, very romantic idea. I've often thought how the sterile transaction of cash entitles me to privacy wherever I go, its attractive but lifeless.
It was a great experience although I was helped by a tax refund that appeared in my bank a/c and had a small 'buy me a coffee' site for friends following the walk.
Like the French man you mentioned, I met two walkers who carried no money and seemed to be permanently on the road... there was a real sense of peace from them. I don't think I could do that though.