Siena itinerary

Rent a car to access the small towns and villages easily. In November, crowds will less. Enjoy Tuscany!
On or off of the historic SR 222, called the Chiantigiana, between Siena and Florence, visit Panzano, Castellina, Greve, and Radda.
To the SE of Siena, Montalcino and Pienza.
To the west of Siena, San Gimignano and Volterra.

So many to choose from.... don't forget Lucca!

There's a Hertz office located just down the street from the train station in Siena that's quite convenient. Note that it's closed between 1230 - 1530 every day, and is closed on Sunday.
Parking is available at the underground lot at the train station for 2 Euros per day - one of the best deals you'll find in Italy.

Luca, Montepulciano, Cortina, Assisi........loved them ALL

Siena and Lucca are two of my favorite towns. Enjoy!

Taking the Baltor bus from Rome Tiburtina to Siena will save you around 1 hour travel time over the train.

Use https://www.rome2rio.com/map/Rome/Siena

We usually visit 2, sometimes 3 towns a day while driving. We lay out our visits by heading to the furthest location first and working our way back to our base. All the locations mentioned are worth visiting. Use the above site to plot out your routes.

Thank you everyone for the suggestions! I’m really looking forward to the trip.

Lisa

Second vote for Castellina in Chianti. It was one of my favorites!