01Stop · Start
Wine Tasting·Italy
Castellina in Chianti
Historic Chianti Classico village with Etruscan heritage and prestigious wineries.
⌬Etruscan heritage⌬Chianti Classico wines⌬Vineyards⌬Local gastronomy
Slow travel route·🇮🇹 Italy
Tuscany Wine Route – 12-Day Itinerary
Chianti and Brunello Trail
Duration12 days
Stops6 stops
Best timeAutumn — Tuscan harvest, mild weather and quieter villages
CategoriesWine Tasting · Castles · Agritourism
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Castellina in ChiantiThe itinerary
The stops.
6 stops06
02Stop · Midway
Wine Tasting·Italy
Radda in Chianti
Medieval Chianti hilltop village surrounded by Classico vineyards, olive groves, and ancient walls.
⌬Chianti Classico wine⌬Medieval walls⌬Hilltop views⌬Hiking
03Stop · Midway
Wine Tasting·Italy
Gaiole in Chianti
Medieval town in Chianti Classico with historic castles and renowned wine estates.
⌬Chianti Classico wine⌬Medieval architecture⌬Historic castles⌬Olive oil
04Stop · Midway
Wine Tasting·Italy
Buonconvento
Buonconvento is a perfectly preserved medieval walled town in the Val d'Orcia.
⌬Medieval brick walls⌬Strategic wine location⌬Val d'Orcia gateway⌬Hiking
05Stop · Midway
Wine Tasting·Italy
Montalcino
Hilltop town world-famous for Brunello di Montalcino DOCG wine.
⌬Brunello di Montalcino wine⌬Historic architecture⌬Local gastronomy⌬Vineyards
06Stop · End
Wine Tasting·Italy
Montepulciano
Hilltop town famous for Vino Nobile di Montepulciano DOCG and Renaissance architecture.
⌬Vino Nobile di Montepulciano wine⌬Renaissance architecture⌬Historic town square⌬Etruscan history
The shape of it
Route map.
6 stops · 5 legs
Why this route
Highlights of this route.
01
Etruscan tombs and Chianti trails around Castellina
Ancient Etruscan burial chambers dot hills around this stone village amid Chianti Classico vineyards.
02
Castello di Volpaia and the Chiantigiana road from Radda
Medieval fortress overlooks Chianti valleys from this hilltop village on the scenic wine road.
03
Castello di Brolio and Tuscan cooking classes in Gaiole
Iron Baron castle dominates Brolio estate where Tuscan cooking classes use estate olive oil.
04
Medieval walls and Via Francigena at Buonconvento
Thirteenth-century walls protect this Via Francigena pilgrim stop beside wheat fields and vineyards.
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What's actually available to you.
6 stops
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Regions on this route.
1 region
