We're staying at an Airbnb N of Siena for several days and then moving to an Airbnb and hour south of Siena.
We check in late at the southern bnb, so we have a full day with our luggage in the car.
In my preferred choice, I'd look at driving Rick's Tuscany Drive and then going to the bnb.
We'd spend a long day and evening in Siena the day before (Rick says it's a different town when the buses leave).
BUT we'd me more open to luggage theft (multiple locations, ...) than if we were at just one 'good' parking lot in Siena for the full day and then head south from there.
Should we play it safe(er) and just do Siena for the day? (the southern bnb has check-in between 3-8 PM, so we'd have to be on the road early in the evening)
Or are Montepulcino, Pienza, Montalcino and La Foce Gardens places where we can hope for a good parking lot?