Parking options outside Siena and Florence

just did both this summer. For Florence, I parked at Villa Costanza for a few days and took the tram into the historic center. Access is so easy - very well marked exit directly off the highway. The lot is clean, lit, well maintained and presumably monitored. Tram access is a short stroll. And yes, my car was there when I returned, unmolested.

For Siena, I ended up parking in the stadium lot near the top, which was a bit tricky to get to but easy to get out of and quickly out of town without any ZTL hiccups. In hindsight, I'd have parked near the station but I can't advise you on the steps to get into town from there. Edit: by tricky to get into, I mean Google insisted I should drive through a ZTL zone to get there. I refused and had to figure it out for myself. So have your route clearly planned if you go to the stadium lot (which has lots of spaces and a moderate cost.)

Parking at the train station in Siena is pretty straightforward. It's an underground lot, the signage is quite clear, and the cost (in '19 anyway) was 2 Euros per day. We never had any issues with finding an empty spot during a 5 night stay in the city pre-Covid. It's well outside the dreaded ZTL area and getting back on the SR2 roadway is a snap.
Getting up into the city is easy too. Can either take a series of escalators starting from the shopping center located a few steps away from parking or (better I think) just spring for a taxi - cost us about 12 euros for the one-way trip which dropped us off right at the Campo.

Nelly, can you buy tram tickets at the stop?

Also, thanks for the reminder about google maps not always taking you where/how you want to go. I do not want that to happen!

We’ve parked at the Stadio lot in Siena and the Santa Caterina. I think it depends on which area is by your lodging.

For Florence we parked in Villa Costenza.

https://parcheggiovillacostanza.it/en/

I'll admit, after renting a car in Strasbourg last month, I seriously reconsidered trying it in Italy in March since I struggled a bit to find parking outside the little villages along the wine route, but I remember someone saying they scope out all the towns they want to visit ahead of time for parking spaces and make note of them, so that's what I've been working on. I think I've found easy(ish) parking outside or on the edge of various towns I want to visit in the Umbria and Tuscany regions. I've made guides for each little town in google maps on my phone. I'm not that techy, so if it hadn't been mentioned here, I probably wouldn't have thought to do this, so to whomever suggested this, thank you!

It also looks like getting in and out of Chiusi with the rental car is pretty straight forward. Does anyone know if there is a gas station nearby so I can fill the tank before I drop it off?

Although my Airbnb in Orvieto has parking, one of the comments I read said it's hard to find because it doesn't match up with GPS, so I'll probably park in the free lot close to the train station. My Airbnb in Montepulciano is just along the wall and has parking which does not require entering the ZTL zone, so hopefully that will be easy too.

I'll admit, after renting a car in Strasbourg last month, I seriously reconsidered trying it in Italy in March since I struggled a bit to find parking outside the little villages along the wine route...

The problem is, there's no better way to explore Tuscany than by car. I don't know how busy the region will be in March. We went early to mid December pre-covid and had no problems parking. We actually had Radda pretty much to ourselves the morning we visited.

We did a day trip to Siena and parked at the stadium. It was tough to find, Garmin was not helpful. The entrance is tucked away and not plainly marked. I suggest the train station might be a better alternative. It was wonderful, though. That evening we bought roasted chestnuts from a street vendor and munched on them while walking through the old town.

If you have the time, I highly recommend a visit to the Abbey of Monte Oliveto, Schedule your visit for the afternoon and return for Vespers that evening. There's a clip of the monks singing in RS's Holiday Special. When we were there, the only other outside person was a lady from a nearby village. The monks invited us to sit with them and participate in the responses. It was one of the most meaningful experiences during our time in Tuscany.