Chiantigiana (SR222): Florence to Siena
Must-DoIconicThe classic Chianti road through the heart of wine country. Greve in Chianti for the piazza market, Panzano for Dario Cecchini's legendary bistecca, Castellina for wine tastings. Allow half a day minimum.
Val d'Orcia Loop: Pienza – Montalcino – Bagno Vignoni
Must-DoThe UNESCO World Heritage landscape at its finest. The road from Pienza to San Quirico d'Orcia passes the most photographed cypress trees in Italy. Stop in Montalcino for Brunello, end at Bagno Vignoni's hot spring piazza.
Crete Senesi: Asciano to Buonconvento
Hidden GemThe "Tuscan badlands" — clay hills, solitary farmhouses, and an alien landscape south of Siena that most tourists miss. The road through Monte Oliveto Maggiore (a stunning abbey) is the highlight.
Garfagnana Valley: Lucca to Barga
Hidden GemFamilyNorth of Lucca, the Serchio valley cuts between the Apuan Alps and the Apennines. Fortified villages, chestnut forests, and a completely different Tuscany — rural, mountainous, and overlooked. Barga is a gem.
Costa degli Etruschi: Livorno to Populonia
FamilyThe Etruscan coast south of Livorno — pine forests meeting sandy beaches, with the medieval hilltop of Populonia overlooking Elba. Stop at Bolgheri for wine (Sassicaia country) and the famous cypress avenue.
Our pick
The Val d'Orcia loop is non-negotiable. But pair it with the Crete Senesi for the real hidden Tuscany.