The road between Radda and Panzano is called the Chiantigiana, and it runs for about twenty kilometers through the heart of the Chianti Classico zone. It is not a difficult road to drive. It is a difficult road to drive slowly enough. The views — Cypress-lined roads cutting through rolling hills of vineyard, olive grove, and forest — are the kind that have been photographed so many times that the real landscape somehow still exceeds expectations.
Radda is the smaller of the two villages, and it feels it. The medieval stone walls that still encircle the town were built to keep people out, and the feeling persists. There are fewer restaurants, fewer wine shops, fewer signs pointing to wineries. There is also, notably, less of the slightly desperate tourism infrastructure that afflicts Panzano in high season. Radda takes its time.
Panzano is more accessible, which means more crowded in summer and more likely to have a restaurant open on a Tuesday evening in February. It also has the advantage of being surrounded by some of the best Sangiovese vineyards in all of Chianti Classico. The Conca d’Oro — the Golden Basin — is the valley south of Panzano that many producers consider the finest terroir in the zone. The wines from here have a combination of structure, elegance, and terroir character that is difficult to find elsewhere.
Where to Drink
In Radda, the obvious stop is Volpaia. The town itself is a fortified medieval village — essentially a film set that happens to have 300 residents — and the Volpaia cooperative produces consistently excellent Chianti Classico from vineyards surrounding the town. The Induezo Riserva is the wine to look for: deep, structured, and serious.
Also in Radda, seek out Montevertine. This is one of the few major Chianti producers that has never declassified to IGT, even when doing so would have been commercially advantageous. The Montevertine Riserva has a purity and directness that stands out in a region where Sangiovese is too often buried under oak.
In Panzano, the essential stop is Fontodi. The estate is run by the Manetti family, who have farmed the Conca d’Oro since the 1960s with an increasingly biodynamic approach. The Flaccianello della Pieve is their top wine — 100% Sangiovese from their best parcels — and it is one of the most powerful, age-worthy expressions of Sangiovese produced anywhere. It is worth seeking out, and it is worth drinking with some patience: the young bottles are impressive, the ten-year-old bottles are extraordinary.
At the other end of the quality and price spectrum, Fontodizio is Fontodi’s entry-level Chianti Classico and one of the best value wines in the zone. If you find it in a wine shop, buy it.
Where to Eat
The trattorias in this part of Chianti are not trying to impress you with novelty. They are trying to feed you well, and they mostly succeed.
Trattoria Le Panzanelle in Panzano is the reliable choice: a wood-fired grill, good bistecca alla fiorentina, solid house Chianti. Book ahead in summer.
In Radda, Osteria Le Panzacce is smaller and more serious. The pasta — pappardelle with wild boar ragù, or pici cacio e pepe — is worth the drive alone. The wine list skews local and is reasonably priced.
The Practical Advice
The Chiantigiana is a day trip from Florence if you leave early and plan your route. But it is better as an overnight, ideally two nights split between the two villages. The roads are narrow and the wineries are spread out; you will not cover them in a single day, and rushing through a Chianti tasting defeats the purpose of being there.
Bring comfortable walking shoes. The villages are medieval; the streets were not designed for people who are in a hurry.
