Rome to Florence - Road Trip - advice gratefully accepted

Hi and welcome to the forum!
First question Have you driven in Italy before, or have you explored the differences you need to be aware of before you do? Apologies if you know what's involved but worth the question so we can steer you to some helpful resources regarding signs, no-drive zones (ZTLs) etc. if applicable. :O)

Will you be dropping the car once you reach Florence? You will not need it or want it there!
If so- be sure to check the hours rental agency is open for drop off.

Will you be staying in Florence and if so do you have any day trips planned from Florence?

We have stayed in Siena, Orvieto and Montepulciano and all are lovely and worth a few nights.
Looks like you have 4 nights? Would you consider two 2 night stays?
The issue you will have is parking and car access to any of the above towns. All have ZTLs, very limited lodging with parking.

I can recommend hotels we stayed that do have parking if you are interested in Orvieto, Pienza (we like better than Montepulciano for overnight as it is easier to access) Montepulciano and Siena.

Thanks for the quick replies!

We’ve ridden in Italy on motorcycle road trips so rules etc are familiar but this is our first time to worry about parking a car. We’re aware (in general terms) of limited parking in many places.

We’ve timed our dep/arr to ensure easy pick-up and drop-off.

We’d happily consider two two-night stays to maximize our time in particular places.

Sorry - and we will be staying in FLR for another six days. Cheers!

We’ve ridden in Italy on motorcycle road trips so rules etc are
familiar but this is our first time to worry about parking a car.
We’re aware (in general terms) of limited parking in many places.

Excellent. Thanks for providing that useful detail!

OK- good info

Make sure all drivers have an IDP- International Driving Permit- it is required by law. Get at AAA before you leave US- assuming you are coming from US?

Read up on ZTLs, parking. You will not be driving IN to any of these hill towns, parking is in lots outside the walls. Make sure your luggage is well hidden whenever you stop along the way. Take valuables with you. Hide your luggage before you park.

Siena is easily done as a day trip from Florence- by bus- quicker and easier than train. But it is especially enchanting in the evening as well so you will need to decide if Siena gets an overnight or not.

Lodging with parking/easy access by car

Orvieto- visit Civita di Bagnoreggio on the way to or from

Hotel Duomo has parking. Very nice family run hotel right next to Duomo they will actually park your car for you.
https://www.orvietohotelduomo.com/

Pienza
Piccolo Hotel del Valle or Hotel Gregorio
https://piccolohotellavalle.com/en
https://www.hotelsangregorio.it/en/

Both onsite parking
Both easy quick walk into village
Piccolo has absolutely fantastic view.

Montepulciano- we stayed here in 2014- it was fairly new. Since then we have stayed in Pienza- well- because it is flat. Montepulciano is very very steep!
Palazzo Carletti
https://palazzocarletti.it/en/
Parking is down the hill below hotel. Great location, beautiful rooms

Siena
Palazzo Ravizzi or Hotel Athena- next door to each other- both share fantastic view
Quick walk to Il Campo
https://palazzoravizza.it/
https://www.hotelathena.com/en/

If you don’t mind a 1 night stay, I might do 1 night in Orvieto then 3 in Pienza or Montepulciano. While there you can day trip around the gorgeous Val D’Orcia.

ETA
Yikes! Just realized you are going in just over a week? Lodging is going to be limited- I'd get right on Booking.com and see what is available. Use the filters for parking, AC, budget etc.

The SS2 from San Quirico to Siena is very scenic as it goes through the unique hills called the Crete Senese https://en.wikipedia.org/wiki/Crete_Senesi. The town of Pitigliano is uniquely located and the views when approached from the west are super. It's worth a short stop to explore and perhaps visit the unique Jewish historic sites. Civita di Bagnoregio is memorably excellent, but the immediate area is not especially overnight worthy.

We just came back from a Road Scholar tour of Tuscany and Umbria staying five nights in Siena and doing day trips to great medieval towns.

Parking is a huge problem to visit just about any place that you want to see. Plan ahead, do your research.
The roads you will use will be curvy and slow. Plan your trip time between cities, it will take longer than you think.
Enjoy, this is a wonderful area of Italy.

Thank you Everyone for the great information! I have an IDP from a Himalayas ride last year, so accommodation is the last thing for us to organise.

Be sure to check which countries your iDP covers and check the expiration date-they do expire

Yes - all good! TY.