The landscape and roads of the middle ages were significantly different than what we have today. Villages were separated from one another by forests, water, mountains, or grasslands so your route was determined by available paths (percorso). The paths, or streets/highways were almost never paved and varied in width and condition based on their length and usage. Bridges made of wood or masonry were the only options for crossing deep waterways.
To make a journey on foot one would need a good pair of shoes and a bag (borso) to hold food, blanket, and coins or something of value for trade. Water or wine could be put into a flask (borracce) and refilled in streams or at taverns along the way. If one was transporting goods, a mule was the next cheapest option, evidenced in frescos of Ambrogio Lorenzetti 1338-1339.
Viaggiare nel Medioevo by Hans Peyer, 2009
Il Viaggio Nel Medioevo by Jean Verdon, 2001