01Stop · Start
Photo: BetacommandBot · CC BY-SA 3.0
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 ChiantiPhoto: “Castellina in Chianti” by BetacommandBot, CC BY-SA 3.0, via Wikimedia Commons. Resized; cropped to fit the layout. Shared under the same licence.
The itinerary
The stops.
6 stops06
02Stop · Midway
Photo: Kasa Fue · CC BY-SA 4.0
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
Photo: Adbar · CC BY-SA 3.0
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
Photo: LigaDue · CC BY-SA 4.0
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
Photo: Chensiyuan · CC BY-SA 4.0
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.
Book your experience
What's actually available to you.
6 stops
Zoom out
Regions on this route.
1 region
Photo: Waugsberg · CC BY-SA 3.0
Italy38 destinations
Tuscany
Tuscany, known for its rolling hills and rich history, is the second-largest region in Italy. Florence, its capital, is renowned for Renaissance art and architecture, but also worth exploring are smaller towns like Pienza, famous for pecorino cheese, and San Gimignano, known for its medieval towers. The region boasts diverse landscapes from the Chianti vineyards to the coastal Maremma. Tuscany is also celebrated for its local festivals, such as the Palio di Siena, and its traditional cuisine that emphasizes fresh, local ingredients. This area offers a glimpse into Italy's agrarian past with its rustic farms and olive groves, making it a unique place to slow down and connect with the local culture.
Wine TastingThermal SpasHikingAgritourism
Images on this page
- Photo: “Castellina in Chianti” by BetacommandBot, CC BY-SA 3.0, via Wikimedia Commons. Resized; cropped to fit the layout. Shared under the same licence.
- Photo: “Radda Chianti Sept 2021 3” by Kasa Fue, CC BY-SA 4.0, via Wikimedia Commons. Resized; cropped to fit the layout. Shared under the same licence.
- Photo: “Wine-growing holding in the Chianti region” by Adbar, CC BY-SA 3.0, via Wikimedia Commons. Resized; cropped to fit the layout. Shared under the same licence.
- Photo: “BuonconventoPanorama4” by LigaDue, CC BY-SA 4.0, via Wikimedia Commons. Resized; cropped to fit the layout. Shared under the same licence.
- Photo: “A view from Montalcino (5772034130)” by Michal Osmenda from Brussels, Belgium, CC BY-SA 2.0, via Wikimedia Commons. Resized; cropped to fit the layout. Shared under the same licence.
- Photo: “1 montepulciano aerial 2024” by Chensiyuan, CC BY-SA 4.0, via Wikimedia Commons. Resized; cropped to fit the layout. Shared under the same licence.
- Photo: “Cascate del Gorello a Saturnia” by Waugsberg, CC BY-SA 3.0, via Wikimedia Commons. Resized; cropped to fit the layout. Shared under the same licence.