The ancient Via Cassia (II century BC) was built by the Romans on pre-existing Etruscan routes in order to connect Rome with Florence. This must not be confounded, as is sometimes done, with the former highway 2 Via Cassia (SS2) – now called Via Cassia 2 (SR 2), for the ancient Roman Consular Road passed through Arezzo, the other runs across Siena and a number of splendid medieval towns and villages.
The route can be done in a single day (approximately a 6-hour drive) or you can take it slowly and stop along the way.
Just in case, these are the places you shouldn't miss: Castellina in Chianti, Monteriggioni, Siena, Buonconvento, San Quirico d'Orcia, Bagno Vignoni, Castiglione d'Orcia, Radicofani, Abbadia San Salvatore, Acquapendente, Bolsena, Montefiascone and Viterbo.
If you have only one day, you can consider a Tuscany tour and visit Monteriggioni, Radicofani and Abbadia San Salvatore. If you have a weekend, you can spend a whole day in Siena or in Val d'Orcia.
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