Franciscan Chronicler Salimbene de Adam describes a particularly dangerous period in Northern Italy between 1248 and 1252 thusly:

"And thus there was a bitter war in those days [following the liberation of Parma] which lasted for many years and men could not plow, nor plant, nor reap, nor plant vineyards, nor harvest the grapes, nor even live in villages… Indeed, men did their necessary work near the cities under guard by civil troops… Such procedures were necessary because of the huge number of bandits, thieves, and predators… These men were crueler than demons… and so it was that a man would far rather meet a devil on the road than another man."

My opinion is that even at the best of times, traveling country roads far from home could be quite dangerous, but when a region was in a state of war it verged upon suicidal. That being said, different authorities kept different levels of control over different regions, and I'm sure certain areas were pretty safe if their local lord was able to keep a handle on lawlessness.