Tuscany, driving/parking in medieval cities?

It's easy and usually well indicated. If I don't put a specific parking in my GPS, I usually follow the signs to bring to the old part of the towns and then you start seeing indications of parkings.
Your choice of villages and cities is very good and try to add Pienza and Montepulciano. I find this area to be the most Tuscan of all.
In Orvieto(going there in a month) all books say to park here and then take the funicular to the old city:
https://www.google.ca/maps/place/Parcheggio+Orvieto+Percorso+Meccanizzato/@42.7152893,12.1042483,16.56z/data=!4m8!1m2!2m1!1sOrvieto+parking!3m4!1s0x0:0x78a62f6bc557d459!8m2!3d42.7166768!4d12.1051613
In Lucca, there are multiple parkings just outside the walls. Just go on google maps and write Lucca parking. Many will pop up.
I parked in one of those in 2007, didn't have a GPS and followed signs to the touristic area.
And the same with the other cities mentionned.
Have a great trip
Claude

Luca and San Gimignano- park right outside city walls. Volterra has an underground lot you can access before town , from Road that goes up the hill. Castellina-Rt 222 goes through town, look for parking spaces.

As I recall, S. Gimignano has parking just outside its walls, with a not overly taxing walk in. The advice you just got on Orvieto is spot on. I think I remember underground parking just outside Volterra. Your including Civita suggests you are unclear on the concept. Think of a dry island connected to the mainland by a pedestrian-only bridge. Yo,u have to park in Bagnoregio. Personally, I don't think it's worth the effort.

Thanks for the tips so far folks.

We are staying in Montepulciano (with a pass to drive into the town) and Panzano for four nights each after Florence. and exploring from those towns. Have other towns on our list too. cheers. Peter

Re Civita, we parked around the Cafe Belvedere, free at the time. There is also parking directly under the bridge. Got lost in Siena, ended up with metered street parking outside the gate closest to the university botanical gardens. Cortona, street parking on Via Battisti close to the main park on the hill, can't remember if we had to pay or not.

First follow signs to the City center, often symbolized by this sign

Make sure you don't go thru these sign, respectively meaning No Motor vehicles permitted

Or Do not enter.

The former is used before a ZTL (limited traffic zone), the latter is used before entering a bus only lane.

As you get near the city center you will see plenty of these Parking signs

If you want to find parking lots in any city before hand just Google Parcheggi followed by the name of the city or town.

There are no rental offices at the Florence station, they are all on Via Borgo Ognissanti, about 10 min walk away.

Lucca is somewhat out of the way from your bases. It would be best to visit by train while you are staying in Florence, if you have an extra day to spare in Florence.

Yes, I mean the one on Via Borgo Ognissanti. close to the (Firenze Santa Maria Novella ) train station

Hertz or Avis or WinRent (SIXT): Via Borgo Ognissanti, 500 metres from Santa Maria Novella Railway Station. . Our hotel has a shuttle to the train station and I assume they can drop us off there to pick up the car.

Map to walk from one of the car rental companies to the train station: 7 minutes, https://www.google.com/maps/dir/Firenze+Santa+Maria+Novella,+Stazione+Ferroviaria,+Piazza+Santa+Maria+Novella,+50123+Firenze,+Italy/Win+Rent,+Via+Borgo+Ognissanti,+96,+presso+Garage+Europa,+50127+Firenze,+Italy/@43.7757201,11.2426875,16.32z/data=!4m14!4m13!1m5!1m1!1s0x132a56a5110a5089:0x1958e826bdc6c329!2m2!1d11.2478839!2d43.7765223!1m5!1m1!1s0x132a56a90b1ea015:0x7ee37fb2a521e3be!2m2!1d11.243673!2d43.773989!5i1?hl=en