Which is better for a base

The overwhelming majority of Rick Steves' followers choose Montepulciano because that is what the Maestro recommends and that is where most people in this forum have stayed. So that is the majority of recommendations you will get here.

I can only tell you that the best base(s) will depend on which towns you want to visit during your stay. List them and I will give you my 5 cents. Montepulciano area is good if you want to visit that area of Tuscany and parts of Umbria.

Completely agree with Roberto.
Just got back from my second trip in that region and i was staying 5 minutes from Buonconvento. Perfect for the towns I wanted to see, siena, san G, volterra, monterigionni, montepulciano, montalcino, pienza. I saw Orvieto on my way up from Rome.
10 years ago i stayed in colle di val d'elsa north of siena because i had gone to Florence only for a day. But i was too far frrom the region that I prefer, which is around buonconvento, pienza and Montepulciano. The road between san Quirico and pienza and montepulciano is a must.

Thank you so much for your replies! Roberto, I am currently working on my list of cities we want to see. In the mean time - out of which city is it best to rent a car - again, we'll be flying into Rome. My original thought was to use Orvieto as our first base, renting a car there and staying in Montepulciano for our second base. Thoughts?

Grazie

If, when you arrive at FCO, plan to immediately go to Umbria/Tuscany (i.e. Without spending any time in Rome upon arrival), then you could consider renting a car at the airport and head to Orvieto. Orvieto itself can be visited in a few hours, but if you have a car while there, you can venture to the surrounding areas, like Todi, Civita, etc.

You could be going there by train, then rent a car in Orvieto (only Hertz is in town however), but renting at the airport is easy enough. If you have done so in any North American airport, it is not any different at FCO. I know there are people who will suggest here to travel 80 miles from the airport to Orvieto by taking two trains, with the luggage and all, then rent the car in Orvieto. That would be equivalent to someone headed to Santa Inez valley and Santa Barbara, California, landing at LAX, then taking Metrolink and Amtrak trains to Santa Barbara, to rent a car in Santa Barbara, instead of renting the car directly at LAX. Who does that? Someone has to tell me, who the hell does that?

I agree with Roberto. If you are flying in to FCO, just rent the car there. It's easy to drive from the airport to Tuscany. You won't be going through Rome you'll drive the first part of the trip on the divided highways. This also makes the return easy. We drove back the day before we were to fly home. We stayed at the Hilton at the airport and took their free shuttle into the city. There we took the Walks of Italy evening stroll that covers the Pantheon, Trevi Fountain, part of the Via del Corso, Spanish Steps and Piazza Navona.

Where you stay is a matter of what you want to see. If you want to see San Gimignano, Volterra, Siena and maybe Pisa/Lucca and the lovely SR222 drive, stay in the Chianti region. Consider an agriturismo. We loved staying in one. If you want a little more action, stay in one of the villages. I wouldn't recommend a big city where having a car would be cumbersome.

Do you have a compelling reason to go to Bologna? It is much further north. It's too far for a day trip and you would burn up 3 of your 10 days getting there, spending a day and then returning.

I'd give your side trip a miss, go with a base in the Val d'Orcia and one in the Chianti region. Montepulciano - I've never read a Rick Steves book, I saw his video clip a few years after we had been the first time - is a good bet for the former. If you want something smaller then Pienza, San Quirico or Cetona. For Chianti, the decent but often overlooked Barberino is a good central base and has easy access to Florence by bus. Don't drive into central Florence, I don't know if there is a convenient lot or location on the outskirts. I believe buses also run from Greve and Panzano.

There is only one large city, Florence, followed by the popular, smaller cities of Lucca, Pisa and Siena. The rest of the main area is made up small towns or villages. I would not base with a car in a city. If you want to stick to one base only, maybe a farm stay close to Siena, if you don"t mind driving out for supper.

Whatever you decide on, try renting apartments. They usually rent by the week during the busy season, I don't know when you are going.

Okay... my trip is FINALLY coming together - I just have a few more questions to ask of you VERY kind people.
1. I know driving in Florence is a nightmare, is it possible to leave our car behind at the train station while we explore Florence for a - or is that just not a good idea.
2. What hotels would you recommend near FCO/ reasonably priced.

Thank you soooo much!!!

Okay... my trip is FINALLY coming together - I just have a few more questions to ask of you VERY kind people.
1. I know driving in Florence is a nightmare, is it possible to leave our car behind at the train station while we explore Florence for a - or is that just not a good idea.
2. What hotels would you recommend near FCO/ reasonably priced.

1. We looked into driving into Florence and after talking to the staff at our agriturismo, we decided to take the bus. We were staying just outside Greve. There's a great public lot in Greve that's free. We just caught the bus and rode in. We made one transfer and arrived at Piazza San Marco where our Walks of Italy tour started. I'd look into parking in the suburbs and catching a bus. From what I can tell, you'll have to go through congestion just to get to the train station. I hope Roberto replies with more detailed information.

2. We explored our options and decided to spend just a little more and stay at the FCO Hilton. It's very nice and extremely convenient. Since I stay at Hilton properties when traveling for work, we got a free upgrade to the executive floor. There's a small dining area on that floor that offers a free breakfast. We had a nice breakfast and instead of taking their shuttle, we just walked over to the terminal.

Also, the FCO Hilton provides a free shuttle to Rome. We checked in, then took the 3:30 shuttle to Rome where we took a wonderful Walks of Italy Evening Stroll. We finished in plenty of time to catch the 10:00 shuttle back to the hotel.

1. Which train station? Florence SMN train station is in the city center and not quick to reach coming from the south. Below are the available options:
   A. Drive to Florence at the often suggested PARCHEGGIO OLTRARNO. It's relatively easy to reach and walking distance to the sights. I can't give exact directions since I don't know where you are staying. Just look on Google Maps. It's next to Piazzale di Porta Romana, on the inside of the wall. Set your GPS. Check the description linked above.
   B. PARKING VILLA COSTANZA. This is a brand new option, that just opened. This parking option is accessible directly from the freeway (it's along the freeway). It has its own A1 freeway exit called PARCHEGGIO VILLA COSTANZA between FIRENZE IMPRUNETA and FIRENZE SCANDICCI exits. The freeway exit is only for the parking lot. From there take the light rail tramway to the city center (line 1 goes to the SMN central station).
   C. Depending on where you are staying there might be a train or bus that you can take. Once you tell me your exact accommodations address, I can suggest.
   If you drive and park to the city, the new option B above, is probably easiest if you are scared to drive in city streets.

2. Hilton at FCO is great. Not cheap, but convenient if you have an early flight. Just walk to the terminal through the skywalk. The car rental returns are also accessible by the same sky walk. Car rental is in the parking structures. Car park tower A for Avis, Hertz, Car park tower B for Europcar, just to name a few.
   Hilton at FCO is not convenient for visiting the city of Rome, if you stay multiple days, since the airport is far from the city center, but it's great for the last night before an early morning flight.