There is a road that runs straight as a stretched string from Sansepolcro, in the Tuscan Valtiberina, across the valley and then steeply uphill to the most perfect Italian hilltown you are ever likely to visit. There are magnificent medieval walls, towers, cobbled lanes, arched passages, stairs, and views over the countryside. Although tourists are few, the town is famous, because of what happened down the hill, along the same straight road, long ago.
Piazza Baldaccio boasts an excellent gelateria, and splendid views of the valley below. You can eat your ice cream, and imagine the scene on 29 June, 1440, when the brave Florentine soldiers defeated the fearsome Milanese in a titanic struggle. Or so it was said. It lives in history as the Battle of Anghiari.
Actually, according to Niccolo Machiavelli, it was a fairly sedate event lasting four hours, between hired armies on both sides, in which the only casualty was a man who fell off his horse. Machiavelli disliked mercenary armies, who often waged their battles carefully, to fight (and get paid) another day. Possibly Niccolo was exaggerating to make a point. There is a museum in town about the battle; you can decide for yourself.