During the millenarian history of the Via Etrusca, many people have passed through it and among them one of the greatest generals of antiquity: Hannibal Barca. It is the Second Punic War: After the winter victories of 217 BC in the Po Valley, Hannibal has Rome as his target. The obstacles for the Carthaginian are the consular troops located in Rimini and Arezzo which, if merged, would defeat him. For this reason, in the spring the African leader crossed the Apennines so as not to reveal to the Roman troops about the route he would have taken, whether to Arezzo or Rimini, so that the legions would wait in fortified positions to protect the two cities.
He chose to march towards Arezzo and arrived in Val di Sieve, with a very fast march of four days, finding himself to choose between two paths to reach for Arretium: a long and comfortable one, the across Valdarno – the future Via Cassia Vetus – which although easier was well garrisoned by the troops of the consul Gaius Flaminio Nepote; the other, shorter but harsher – in which the Arno overflowed in those days -, that is the road to the Casentino on the ancient Via Etrusca of Londa. Hannibal chose to take the second path: in June 217 BC. these valleys saw the passage of the Carthaginian army, consisting of about 40,000 men. Hannibal’s choice to pass from the Via Etrusca was fundamental to his strategy: when he arrived in Arezzo he surprised the consular troops, laid waste on the Valdarno, and defeated the Romans in the epic battle of Lake Trasimeno.
In 1440 the Florence of the Medici was at war with the Visconti of Milan, who moved against them the fearsome troops of Niccolò Piccinino. The Visconti troops reached the Mugello valley in April of 1440 and the rival families of the Medici had to decide whom to support; among these was the count Francesco Guidi, Lord of Poppi, whose family up to a hundred years earlier also dominated the territories of Londa.
The Count had to choose who to side with: he wrote to Niccolò Piccinino inviting him to go to Casentino where he would welcome him; he also wrote to Cosimo De’Medici providing information on the progress of the enemy troops. Finally, perhaps due to the resentment he harbored, fearing the expansionist aims of Florence, the Guidi openly supported Piccinino who traveled with the army from the ancient Via Etrusca to reach it in Casentino, but not before besieging Dicomano, Londa and San Leolino. Francesco Guidi’s stance was fatal: Piccinino’s troops were defeated in the Battle of Anghiari on 29 June. After the Count’s betrayal, Florence deprived him of his possessions and of the castle of Poppi, effectively marking the end of the great Guidi family.