9 days in Province of Siena Itinerary

9 days in Province of Siena Itinerary

Created using Inspirock Province of Siena travel route planner

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

Route & dates

Start: Windsor
Fly + Drive:  17 h 45 min
San Gimignano
— 1 night
Drive:  1 h 15 min
— 4 nights
Drive:  1 h 15 min
— 2 nights
Drive + Fly:  17 h 45 min
End: Windsor

San Gimignano

San Gimignano ©
A historical gem in the heart of Tuscany, San Gimignano is known as the Town of Fine Towers for its jutting skyline of high city walls.
On the 24th (Tue), don't miss a visit to Piazza della Cisterna, then get to know the fascinating history of Piazza del Duomo, then do a tasting at Guardastelle Vineyard, and finally indulge your senses at some of the top wineries in the area. On the 25th (Wed), you'll have a packed day of sightseeing: contemplate the long history of Historic Centre of San Gimignano, steep yourself in history at Torre Grossa, then do a tasting at Podere La Marronaia- Sosta Alle Colonne, and finally take in the spiritual surroundings of Church of Sant'Agostino.

To see other places to visit, reviews, where to stay, and more tourist information, go to the San Gimignano online vacation planner.

Windsor, Canada to San Gimignano is an approximately 18- hour combination of flight and car. You'll lose 6 hours traveling from Windsor to San Gimignano due to the time zone difference. In July, daytime highs in San Gimignano are 35°C, while nighttime lows are 21°C. Finish your sightseeing early on the 25th (Wed) so you can drive to Asciano.

Things to do in San Gimignano

Historic Sites Wineries Tours
Highlights from your plan
Historic Centre of San Gimignano ©
Historic Centre of San Gimignano
Wine Tours & Tastings
Podere La Marronaia- Sosta Alle Colonne ©
Podere La Marronaia- Sosta Alle Colonne


Asciano ©
Asciano is a comune and hill town in the province of Siena in the Italian region Tuscany. You'll discover tucked-away gems like Crete Senesi and Contucci. You'll find plenty of places to visit near Asciano: Siena (Piazza del Campo, Torre del Mangia, &more), Pienza (Palazzo Piccolomini & Cathedral) and Museo Civico Archeologico delle Acque (in Chianciano Terme). And it doesn't end there: appreciate the views at Val d'Orcia, learn about winemaking at Cantina Fattoria della Talosa, and savor the flavors at Food & Drink.

To find reviews, more things to do, where to stay, and other tourist information, you can read our Asciano trip planning website.

Getting from San Gimignano to Asciano by car takes about 1.5 hours. Other options: do a combination of bus and train; or take a bus. In July in Asciano, expect temperatures between 37°C during the day and 22°C at night. Finish your sightseeing early on the 29th (Sun) so you can travel to Radicofani.

Things to do in Asciano

Tours Historic Sites Parks

Side Trips

Siena, Montepulciano, Pienza, Val d'Orcia, Museo Civico Archeologico delle Acque
Highlights from your plan
Piazza del Campo ©
Piazza del Campo
Crete Senesi ©
Crete Senesi
Val d'Orcia ©
Val d'Orcia


Radicofani ©
Radicofani is a comune in the Province of Siena in the Italian region Tuscany, located in the natural park of Val D' Orcia about 110km southeast of Florence and about 60km southeast of Siena. On the 30th (Mon), take in the architecture and atmosphere at Abbazia San Salvatore, see the interesting displays at Mining Museum Park, then explore the activities along Terme di San Filippo, and finally make a trip to Fortezza di Radicofani.

To see ratings, where to stay, more things to do, and tourist information, read Radicofani trip itinerary builder website.

You can drive from Asciano to Radicofani in an hour. In July, daily temperatures in Radicofani can reach 36°C, while at night they dip to 21°C. You will leave for home on the 31st (Tue).

Things to do in Radicofani

Parks Nature Museums

Side Trips

Abbadia San Salvatore, Terme di San Filippo
Highlights from your plan
Terme di San Filippo ©
Terme di San Filippo
Fortezza di Radicofani ©
Fortezza di Radicofani
Abbazia San Salvatore ©
Abbazia San Salvatore