5 days in Province of Siena Itinerary

5 days in Province of Siena Itinerary

Created using Inspirock Province of Siena Trip Planner

This plan was created by another user. Make it your plan

Route & dates

Start: Dubrovnik
Fly + Bus:  8 h 45 min
— 1 night
Drive:  1 h 15 min
Castiglione D'Orcia
— 3 nights
Drive:  9 h 15 min
End: Dubrovnik


Siena ©
Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.
To find reviews, where to stay, other places to visit, and other tourist information, read our Siena road trip planning tool.

Dubrovnik, Croatia to Siena is an approximately 10- hour combination of flight and bus. You can also do a combination of car and ferry; or do a combination of ferry and train. In April, daytime highs in Siena are 23°C, while nighttime lows are 9°C. Cap off your sightseeing on the 4th (Wed) early enough to go by car to Castiglione D'Orcia.

Things to do in Siena

Historic Sites Museums
Highlights from your plan
Casa di Santa Caterina ©
Casa di Santa Caterina
Duomo di Siena ©
Duomo di Siena
Basilica Cateriniana San Domenico ©
Basilica Cateriniana San Domenico

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. Your inner history buff will appreciate Terme Bagno Vignoni and Val d'Orcia. You'll explore the less-touristy side of things at Historic Centre of the City of Pienza and Terme di San Filippo. Take a break from Castiglione D'Orcia with a short trip to Tempio di San Biagio in Montepulciano, about 44 minutes away. Next up on the itinerary: learn about winemaking at Ciacci Piccolomini d'Aragona, take in the spiritual surroundings of Cathedral, take in the architecture and atmosphere at Cappella della Madonna di Vitaleta, and see the interesting displays at Palazzo Piccolomini.

For traveler tips, where to stay, photos, and more tourist information, refer to the Castiglione D'Orcia route planner.

You can drive from Siena to Castiglione D'Orcia in 1.5 hours. In April in Castiglione D'Orcia, expect temperatures between 23°C during the day and 9°C at night. On the 7th (Sat), wrap the sightseeing up by early afternoon so you can travel back home.

Things to do in Castiglione D'Orcia

Historic Sites Parks Nature

Side Trips

Pienza, Tuscany, Terme Bagno Vignoni, Cappella della Madonna di Vitaleta, Tempio di San Biagio
Highlights from your plan
Cathedral ©
Terme Bagno Vignoni ©
Terme Bagno Vignoni
Val d'Orcia ©
Val d'Orcia