We'll be staying 3 nights in Siena and want to take a couple day trips into the countryside. Please advise your favorite sights, towns, vineyards, restaurants, etc.
We can give you a more useful answer if you tell us: car or public transportation?
We had thought we'd rent a car for the two days we'll be getting into the countryside. Which do you suggest? I'm open for any advice....
I'm a small town advocate. I love Siena but it can be crowded and overwhelming to a small town boy like me. Even a smaller place like Montepulciano can be too big and busy for me.
With 3 city nights in Siena, you might enjoy the contrast of some small town life.
If I were you, I'd take a day to see Pienza and Monticchiello. The towns are close; you can see one from the other. Pienza is an easy half-day. Don't miss the Piccolomini Palace tour.
Monticchiello is beautiful but tiny, just a couple hundred people. It's an easy 90-minute exploration, leaving plenty of time to eat and drive back to Siena.
Both these old walled hill towns have excellent restaurants and both left a life-long impression on me.