Ancient European communication routes.
The trips during the medieval period in Europe took place along the means (roads) constructed by the ancient Romans, which they strove to preserve taking good care them even though the maintenance was pretty bad and the roads were not comfortable to travel on. The streets were mostly simple tracks covered in mud and, in winter, pebble; to reckon with the natural obstacles almost insurmountable, as the Alps that is not crossed usage normal travelling means and almost never in winter. The waterways, with very few bridges and other so few regular ferry services such as the Po in Piacenza, had to mostly be crossed at the ford, with the risk of drowning or at least losing pets and luggage.
Venturing into the woods (and then Europe was literally covered with forests) was always very risky fact you could easily lose the paths poorly signposted, or you could make bad encounters with wild animals (wolves and bears were numerous), or you could encounter criminals of all kinds. There we used quite often waterborne: wheat, salt, wine, traveling on boats along the Rhone, the Seine, the Loire, the Rhine, the Danube. Abbeys and monasteries had flotillas of boats for the transport of goods, and barrels also large.
Usually, the travel paths were composites: a stretch of Roman road, the ferrying a stream, a path through a forest, a stretch of river navigation. In any case, whether it be traveling on foot and that we could afford chariots and horses awareness of the risks to be faced was that those who had to leave for a long trip prepare for it in time, for example by making a will, knowing that he could not return.