2 nights in Volterra, Montalcino, or??
 

I have almost finalized our itinerary and am having trouble with the remaining 2 nights of our 5 night stay in Tuscany. Our Agriturismo is only available for 3 nights, and is located right near Montepulciano and Montalcino. We have 2 nights before heading to Cinque Terre and we have a car. I was thinking about staying in Montalcino, but since we are staying so close to there on our farmhouse, we will most likely visit there during the day (along with Montepulciano). We are looking for a smaller town to stay in but one that still has enough shops, restaurants and things to keep us busy in evening strolling around. Would you still stay in Montalcino even though we could do an easy day trip there from our farmhouse (is it that much of a different feel staying there?), or would you stay in Volterra maybe, which appears to be on the way to La Spezia to experience both? Thoughts and any other recommendations? Thank you!!

Where is your agriturismo located?
Montalcino and Montepulciano are not very close together.

It is North and somewhat between the two - 30 minutes from Montalcino and 54 minutes from Montepulciano...close enough to do day trips to both, but not close enough to stay for dinner and experience either at night, etc.

Also - I know this is opposite of what I said earlier, but another option is just dropping off the car in Siena and saying there for 2 nights and taking the train to Cinque Terre from there. While we are ideally looking to get the feel of a small town for a couple nights we also want at least a day trip to Siena and wondering if it makes more sense to just stay there since it's on the way, and save the small towns for day trips?

Good idea. Staying in Siena inside the walls in the historic center is a treat. At night it's dark and medieval, like being transported back in time. Siena not a huge place but it's very busy during the day, with many daytrippers. But, like many places in Italy, you get a much different feel at night.

But I'd take the bus from central Siena to Florence and walk across the street to the Santa Maria Novella train station for the train to the Cinque Terre. You won't have to get outside the walls of Siena to the train station and you won't have to change trains at Chiusi.

Actually, I would much prefer to go to Volterra on the way to le Cinque Terre plus get a feeling for Etruscan history. But then again, if there is a lot in Siena you want to experience, spending the night would make sense. I think I might want to keep the car however. Look at the real time logistics about when buses and trains leave.

It would be easier to advise if you posted what time of year you are going. There are times of year when Siena is zoo, or Volterra's roads are iffy, and times when it makes more sense to stay in your air conditioned car than deal with 5 hour transits via bus and train.

We will be there 1st and 2nd week of October, and I just noticed we check out of our agriturismo on a Sunday - I haven't researched a lot yet about what is open and closed on Sundays but imagine we might have better luck in a City like Siena finding shops and restaurants open and things to do? Also I am looking into a hotel in Siena that has free parking so yes I agree and think we would just keep the car even if we went there. And considering part of why we want to go there is to visit the Duomo I am assuming we may have to do that on Monday anyway?

Does it have a name--or a link. I know Tuscany well and can help if you just tell me where.

Look at Santa Caterina in Siena---on SS-2 at the Porta Romana gate into Siena---has parking if you ask.