8 days in Province of Siena Itinerary

8 days in Province of Siena Itinerary

Created using Inspirock Province of Siena Trip Planner

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Route & dates

Start: Tallinn
Fly + Drive:  16 h 30 min
Castiglione D'Orcia
— 2 nights
Drive:  1 h 15 min
— 4 nights
Bus + Fly:  9 h 15 min
End: Tallinn

Castiglione D'Orcia

Castiglione D'Orcia ©
Castiglione d'Orcia is a comune (municipality) in the Province of Siena in the Italian region of Tuscany, located about 90km southeast of Florence and about 40km southeast of Siena, in the Val d'Orcia, not far from the Via Cassia.Castiglione d'Orcia borders the following municipalities: Abbadia San Salvatore, Castel del Piano, Montalcino, Pienza, Radicofani, San Quirico d'Orcia, Seggiano.HistoryThe settlement is mentioned for the first time in 714, when it was a possession of the Aldobrandeschi family. Explore hidden gems such as Val d'Orcia and Historic Centre of the City of Pienza. You'll find plenty of places to visit near Castiglione D'Orcia: Montepulciano (Azienda Agricola Ercolani, Tempio di San Biagio, &more) and Museo Civico Archeologico delle Acque (in Chianciano Terme). The adventure continues: learn about winemaking at Podere Il Cocco, don't miss a visit to Piazza Pio II, see the interesting displays at Palazzo Piccolomini, and contemplate the long history of Terme Bagno Vignoni.

For where to stay and tourist information, read Castiglione D'Orcia trip itinerary builder site.

Tallinn, Estonia to Castiglione D'Orcia is an approximately 16.5- hour combination of flight and car. You can also drive. Due to the time zone difference, you'll gain 1 hour traveling from Tallinn to Castiglione D'Orcia. Expect somewhat warmer temperatures when traveling from Tallinn in September; daily highs in Castiglione D'Orcia reach 32°C and lows reach 19°C. Wrap up your sightseeing on the 18th (Mon) to allow time to drive to Siena.

Things to do in Castiglione D'Orcia

Historic Sites Wineries Museums

Side Trips

Montepulciano, Pienza, Tuscany, Montalcino, Terme Bagno Vignoni
Highlights from your plan
Val d'Orcia ©
Val d'Orcia
Podere Il Cocco ©
Podere Il Cocco
Terme Bagno Vignoni ©
Terme Bagno Vignoni


Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.
You'll discover tucked-away gems like Facciatone and Guardastelle Vineyard. Go for a jaunt from Siena to Chiusdino to see Eremo di Montesiepi about 36 minutes away. There's much more to do: awaken your taste buds at some of the top wineries in the area, admire the masterpieces at Museo dell'Opera Metropolitana, take in the spiritual surroundings of San Francesco, and get lost in a book at Biblioteca Piccolomini.

To see where to stay, maps, and other tourist information, refer to the Siena journey site.

You can drive from Castiglione D'Orcia to Siena in 1.5 hours. In September, daytime highs in Siena are 32°C, while nighttime lows are 19°C. Wrap up your sightseeing by early afternoon on the 22nd (Fri) to allow time for travel back home.

Things to do in Siena

Historic Sites Tours Wineries

Side Trips

Guardastelle Vineyard, Eremo di Montesiepi
Highlights from your plan
Wine Tours & Tastings
Duomo di Siena ©
Duomo di Siena
Facciatone ©