Looking for a small town that would act as a good base for 3 nights to explore a portion of Tuscany, specifically the area between Florence and Sienna heading west. We have 3-4 nights set aside for Florence as well as a night in Siena that would be separate from the 3 nights in Tuscany region I mentioned . I'm thinking of picking up a car in Siena at the end of our stay in Siena. Some of the towns we are interested in are Monteriggioni, Volterra, San Gimiganao, and possibly returning the car to Lucca/Pisa area and then carrying on with the rest of or trip. And any suggestions in this area that would be good for a family of 5 (2 adults, 1 grandparent, 13yo & 9yo).
We were just in Lucca and sorry to say but we didn’t care much for it. Not sure why but just didn’t see the charm that is often mentioned.
Kids might like riding bikes on the wall though
It’s also not a good base, a bit too far west but it is a good place to drop your car.
Monteriggioni is teeny tiny.
With a car you could base outside of SG.
Where are you headed after this?
We prefer the Val D’Orcia region - Pienza, Montepulciano, Montalcino.
Why don't you stay in Siena for the entire stay? Siena is good as a base to visit all the places you mentioned plus more, like the Val D'Orcia, and even Cortona or Assisi. I see no reason to change accommodations to move just half hour away. From Siena you can be in all those places in 30-50 min. Colle Val D'Elsa would be the most central to all the places you listed, but it's only 20 min from Siena, you wouldn't save much time. Just make sure your accommodations in Siena have a place to park on premises or nearby, so that you can utilize your car from there. Some areas of Siena are in the restricted traffic zone.
I trust you know there isn't a single, definite answer to your question. The Search box here works pretty well, I suggest that you look at a lot of similar questions before deciding.
ChristineH - we are likely heading to the Cinque Terra area afterwards.
Robert - for whatever reason I hadn't considered using Siena as a base. And like both you and ChristineH are saying about the Val D'Orcia region, Siena may provide to be a good access point to both areas. Before our April 2020 trip was cancelled, we had a place in Siena just outside the walls near the Basilica di San Francesco. I'll have to find the place and see about parking.
There is public parking at the Basilica of San Francesco in case that hotel does not provide parking. It's not free but what is free these days?
Geo location here:
The historic route SS 222 goes from Siena to Florence, passing by charming Chianti towns such as Castellina, Radda, Panzano, Greve. This route is named the Chiantigianna. Highly recommended. We have stayed along this four times and enjoy how green it is and visiting all the small wineries.
In Lucca, make sure you stay inside the walls. Our hotel, Hotel Palazzo Alexander, offered parking nearby and their staff parked it for us.,