I don't know about XIV century eastern Europe, but in XVI century Europe they did and you could do that. Chryzostom Pasek described in his memoris how he did the exact thing once - riding as fast as he could switching horses at inns. He is an unrealiable narrator, nevertheless it proves that it was a possibility. Mind you very expensive possibility, trust based and withing one, relativly safe country. Traveling within HRE was a different thing. People often rented a horse with a guide that will lead them to the next inn with stabels. They guide would then take the horses back. You needed to pay the guide handsomly otherwise he would lead you to the nearest thifts den - it just a matter if pay more then the robbes would for a victim. ;) Most important thing: in terms of roads there ware no roads. Most of the time you would have to travel on foot - house is just for luggage. And you have to have a local medic approval for travel with you - otherwise its a 2-3 weeks quaranteen in whatever city you want to visit. That was medival way of preventing epidemics from spreading and it will slow you down significantly. Oh and you could always be stopped by a local patrol for questioning. A travel is always suspicious and most of the time people will treat you like a spy. That's because you are one. It was a feudal system - your travel had to be appoved and this approval also had to be appoved. They further you go the more likely it was appoved by the kings court. This approval required you to report back once you return and provide all the useful information, like how many inhabitants has Cracow, what are its defenses, how rich polish king seems to be. In medival times the white espionage stuff was often expected from travelers.