We'll be staying near Siena for 15 days (not counting travel) in October, and we'll have a car. We plan to spend 2-3 days in Florence, the same in Siena, and the same loafing around the countryside, weather permitting. That leaves about 8 days for day trips. My research came up with the possibilities below. I'd appreciate recommendations to whittle the list down to 6 - 8 or so.
- Val d’Orcia loop: Pienza + San Quirico d’Orcia
- Montepulciano
- Montalcino & Abbey
- San Gimignano
- Monteriggioni
- Volterra
- Castiglione della Pescaia
- Colle di Val d’Elsa
- Cortona (since we had the best pizza ever in a small bakery there 23 years ago. It probably no longer exists but we have to try)
The following are described as less crowded and not "touristy":
- Castiglione d'Orcia
- Buonconvento
- Asciano + Crete Senesi
- Radicofani
- Lucignano
- Castel del Piano
These are a bit beyond our preferred 90-minute drive time:
- Arezzo
- Pitigliano
- Lucca
We were in Tuscany 10 days in 2003 and did visit Montepulciano, San Gimignano, Lucca, Cortano, Pisa, and I think Monteriggioni. But it's been so long that I barely remember them.