We can imagine that Leonardo travelled the roads of Tuscany, from the ancient Roman Via Cassia and Via Aurelia to the more recent medieval roadways of the Via Francigena and other routes of pilgrimage and trade.

He undoubtedly had occasion to traverse Tuscany in his journeys to Milan, where he stayed at the time of the Sforza government and during the French occupation; in his reconnoitering through Tuscany, Umbria, the Marche and Romagna as "Architect and Engineer" plenipotentiary to Cesare Borgia; and in his journeys to Rome at the side of Giuliano de’ Medici, the brother of Pope Leo X.

Frequently he traveled on horseback, calculating the distances and measuring them with the odometer or with optical instruments of orientation.

In at least one case the cost estimate for transporting his baggage from Milan to Florence and from Florence to Rome is documented.

Of the many trips undoubtedly made or planned by Leonardo, indications of the route have survived only in a few cases.

The distances reported by Leonardo are expressed in miles; it is hard to say whether this is the Tuscan mile, equivalent to 1653.6 meters, or the Milan mile, equal to 1784.8 meters. Note that the measurements given in parenthesis after each locality refer to its distance from the preceding one.