Best Place to Base in Tuscany and Car Rental Question

If you were to pick up the car in Florence and return it in Orvieto, you could see a whole lot of gorgeous scenery and many beautiful towns in between. RS recommends drives in the Val d'Orcia particularly; DW and I drove them last May, and he was right on (he maps them out in the relevant guides). But there are so many captivating small towns and beautiful roads that you pretty much can't go wrong (as long as you have a GPS!).

For what it is worth, wife and I stayed in San Quirico d'Orcia, which we loved, and which was a fine base of operations. But there are any number of other towns in that general area that would be great places to stay.

Finally, Orvieto is easily worth a one-night stay if you have not been there. It is so beautiful, and the cathedral is wonderful, especially the sculpture on the facade. And it is an easy train ride to Rome from there.

We rented a car in Florence and immediately headed to Tuscany. Drove to, and stayed in, Monepulciano, which we loved. Stopped for lunch along the way. It is winding, so be prepared for that, and it is very picturesque. With three navigators and a driver, you probably won't get lost (and if you do, that's fun too!). We stayed at the beautiful Politian Apartments, inside the gates, and were able to park right outside our apartment. It is a 2 hour drive from there to Rome, so why not keep the car and return it to Rome's Termini Station. When we drove into Rome, we put Google maps on "no highways no tolls" and got a wonderful winding journey through various hill towns. It does lengthen the drive, but you can make it an adventure and stop for lunch along the way.

I don't get the logic of paying for a rental car and still using trains. Costs more, you have to move your luggage more. I guess it avoids the Italy city driving, but really it was not bad as long as you scope out your route ahead of time, and are aware of the ZTL issue.

Have fun!.

Thank you both so much for your helpful replies. I was getting a bit antsy since my Rick Steves Florence and Tuscany guide hadn't arrived yet. I finally received it today. I've only had time to skim through it so far, but I just want to say that your replies are very helpful and I'm going to read them to my husband before we decide as to where to stay, etc.

If you are interested, I can recommend two rentals you may be interested in for your trip. The first is in a small town called Panzano, in the Chianti region. We rented this two-bedroom place last May and it was spacious and comfortable. The owners live on the property but are not intrusive. Here's a link: https://www.airbnb.com/rooms/2278199

The other place is a villa near Castiglione del Lago, which is farther afield but easily reached on the way between Florence and Orvieto. The rental is usually for one week: https://www.vrbo.com/1403458ha?arrivalDate=06%2F04%2F2017&departureDate=06%2F11%2F2017

We're gong back to the villa next Fall. The owner is very responsive and the place is lovely.

Enjoy your trip!

DD

Deidre, thank you for your reply and for those links. I'll be sure to show them to the rest of the family. Both places look lovely.

I have also stayed at the beautiful Politian Apartments in Montepulciano, twice. Both apartments that I rented were absolutely lovely, with gorgeous views out over the countryside, and wonderful owners who answered many questions and helped us to get situated in Montepuliciano. The town is wonderfully located to use as a base for daytripping around Tuscany; I have visited Siena, Montelcino, Volterra, Pienza, and other places using M. as a base. The Politian website gives excellent and (in my experience) accurate photos of each apartment. Parking (as Joan noted) was quite easy; the owners will give you a placard to put in your car window which will give you parking rights just in front of the apartments. Do be SURE to use the directions that they will email to you, with a map, for driving into M. and the apartments. There is a CONAD grocery store at the bottom of the town (the apartments are at the top), and there is a little bus that picks up from near the front of the CONAD that will drop you very near the apartments' door (owner will explain and will sell you tickets for the bus!). I also enjoy the town in the evening; with young adult children along, they may appreciate being able to stroll around to cafes even after the parents are ready to wind down... just a thought.

My favorite spot is also in the val d’orcia/crete senesi region.
Been to Tuscany twice, it’s an amazing region
I was in a fantastic agriturismo very close to buonconvento
http://www.agriturismopoderecunina.com/en
Amazing place, raving reviews, fantastic hosts.
The road, sp146 from san quirico d’orcia, going to pienza, Montepulciano. Then south to la foce, montichiello and back to san quirico is the best of what tuscany can offer.
As for the car, logical to take your car when leaving florence, but when done, you’re going to Rome? Why don’t you drive there, you can stop in Orvieto, you’ll see an amazing village and one of the most impressive cathedral in all Italy. Then just bring the car to probably the termini station where all of the rental companies are, unless you can find somewhere close to your appartment.
As far as medieval towns, the not-to miss would be montepulciano, pienza, san gimignano(do it very early morning or after 4:30 to avoid to feel in a tourist trap). It is a gorgeous village when it’s almost empty. Volterra, sienna for a full day. Montalcino’s fortress is a great place to take spectacular pictures of the surroundings as you can walk on top. Very close the amazing sant antimo abbey. If you have enough time, monte oliveto magiorre is also a great visit. San galgano abbey makes fantastic pictures but is 1 hour west roughly. Perugia in umbria, 1:30 from buonconvento, also has a fantastic piazza, great museum, etc.
You can also think of a one day trip from Florence that would bring to pisa and lucca.

You can return the car in Rome at any Tiburtina station locations. Very close to the Tangenziale Est A24freeway and far from the ZTL. However there are many other options since each rental company has a dozen or so offices in Rome.
If you are in Florence, pick the car up in Florence.

Thank you all again.

I hadn't even paid much attention to the Val d’orcia/crete senesi region. So far, I'd thought of, depending on what type of accommodation is available:

San Gimignano
Monteriggioni
Volterra
Cortona
Montepulciano
Torrita di Siena
Pienza
Anghiari near Arezzo
Castellina in Chianti
Pitigliano
Buonconvento
and finally Lucca or Siena if we get desperate and can't find anywhere to stay.

Thank you also for the car pick up and drop-off tips. You're all so kind and helpful.

Hello!

It is wonderful that you chose Italy.
I love it, I think Tuscany is the best region to visit...

Some suggestions on where to stay:
Volterra, Lucca, Livorno, Versilia, Lucignano

Don't miss the Chianti Region (It's a paradise for any wine enthusiast <3) and the medieval San Gimignano.
Wishing to have the greatest time ever!