Car rental and driving in Tuscan Hill town

Can't help with your first 2 questions, but, for parking on your daytrips, look up public parking lots on Google maps before setting out.
For lunch on your long driving day, since most of it will be on autostradas, I'd save time and just grab a bite at one of the Auto Grills en route. Or maybe Orvieto if you want something 'local'.

Why not pick up your rental car in Sorrento?

or picking it up when you get to Tuscany? Looking at a map, Orvieto might be nice to train to, see the city, grab lunch and then pick up a rental. I just looked at a map and it looks like you will be driving at least 1/4 of the country in that one day. Are you sure it would be quicker to drive?

You probably won't be parking too much WITHIN the hill towns, as they are tiny, sometimes walled, and at times limited to local traffic (ZTL=zona traffico limitado) but as a pp said, look up the addresses of the public parking lots to have a place to be a little more confident on where you can park ahead of time.

I guess I would ask the alternate question [to ChristineH] - which is why drive from Naples past Rome on the freeway rather than the train to someplace more rural and rent a car there. I have done this in Orvieto, but apparently this now limits your vendor option to Herz, and many people do this in Chuisi.

The train from Naples to Rome is much faster than driving that route and all of the driving will be freeway or city traffic which does not strike as something I'd opt into doing. I'd opt to get to the countryside you're interested in seeing and then renting a car for that section of the drive.

Lucca is very charming and I think the tourist influence is minimal - nothing like Siena or San Gimignano - but if you want a working Tuscan hilltown I'd look into Volterra or Arezzo if you want more of a city.

Whatever you decide, have a great trip,
=Tod

My experience is to find the best deal on a rental car and book it (cancellable of course) and then check every so often for a better deal that could be with the same company or a different one. I have also booked with autoeurope.com several times. You have to prepay, but it's fully refundable, usually up to a day in advance. I've done that and got the refund within 48 hours, more than once.

We toured all the southern Tuscany hill towns last year. If coming from Naples, I would take the train to somewhere like Orvieto (get advice from autoeurope or Avis by a phone call) get the car and begin your drive. If traveling in shoulder season, parking in all of these towns is clearly marked and described in Rick Steves travel books. Use his book on Central Italy/hill towns for driving and restaurants. You will love this part of the country. Good choice to stay in a small village as a base.

We trained up from Rome to Orvieto and rented a car there. We based in 2 locations over 8 days. One BB overlooking Monepulcino and the other at Borgo de Carpiano just south og Gubrio. Loved both locations. We had no trouble parking outside of hill town. Also visited Assise. Great trip.

If you are in Sorrento I’d look into renting a car in Sorrento rather than Naples, which is a large city with a notorious chaotic traffic. From Sorrento to the Val D’Orcia it’s largely multilane freeway and the last portion on some rural two lane highway. Sorrento has agencies with the major rental companies. That is what I would do, to save myself the hassle of taking a train and maybe a taxi to Naples then rent there. If you prefer to minimize driving, then you could take a train to Chiusi-Chianciano (change trains in Naples and Rome), which is the town closest to Val D’Orcia with a rental car office (Avis-Budget only).

Check your pricing options on AutoEurope websites below:
www.autoeurope.com
www.autoeurope.eu
www.kemwel.com

I generally book my rental with AutoEurope about a month or so prior to my travel dates (generally I travel to Italy in June/July), but I also booked the car the day before arriving in more than one family emergency situation when I had to fly to Italy immediately. For whatever reason those were the times when I spent less, go figure. I think the things that drive the price of rental, at least with AutoEurope, is the time of they year you travel and the pickup location, not how far in advance you book.

Thanks to all who took the time to reply to me with suggestions and different points of view. I'm still debating, but you've all given me more information to work with. Thank you so much!

I suggest taking the train to Chiusi and renting a car there at the Budget / Avis office right near the train station. From Chiusi, it's an easy drive to Pienza (20 miles / 40 min) on scenic SP146, then maybe another 10 minutes to San Quirico d'Orcia.