Where to stay in "rural" Tuscany

Anyplace in the province of Siena will work.
Orvieto is not in Tuscany and is much further south.

Yes, I know anyplace will work, but need help narrowing it down :) Is Orvieto worth the stop over one of the Tuscan hill towns?

Are you locked into Siena? Siena similar enough to Florence that if you have limited time, I would consider using the Siena time in the countryside. Are you taking the train from Siena to Rome?

Be aware that changing locations and renting a car for just a day will burn up a considerable amount of time. I would consider adding a day to your stay in Siena, then taking a food and wine tour of the Tuscan countryside. That would get you in rural Tuscany for the day.

OH that's an interesting idea. Here is my itinerary idea so far, NOTHING is locked in so I am open to suggestions.

Day 1: Arrive Rome, train to Florence, recover
Day 2: Florence - food tour (sleep in Florence)
Day 3: Florence - Uffizi gallery, Duomo
Day 4: Bike tour Florence to Siena (sleep in Siena)
Day 5: Spend the day in Siena, perhaps San Gmiagano nearby (sleep in Siena)
Day 6: PIck up car near Siena and do self guided drive through the countryside & hill towns (sleep in Montepulciano)
Day 7: Drive Montepulciano - Chiusi (or Orvieto), drop off car, pick up train to Rome (sleep in Rome)
Day 8: 9am flight home from Rome

In your shoes I would sleep in Siena both nights and not bother with changing hotels to Montepulciano for one night only. A lot of time gets wasted when you change hotels (check in, check out, pack, unpack, get familiar with new location). I would look for a hotel in Siena that is car friendly (i.e. outside the ZTL and preferably with parking on premises or nearby). Then I would use that location as your base. During the day I’d take the drive, and in the evenings stroll around Siena.

Sleep in Siena 3 nights and then train to Rome via Chiusi from there? I worry about the drive from Montepulciano back to Siena, just to switch back in the morning to head back South again. Seems like a waste of time - seems easier to sleep halfway between Siena and Rome and then just keep moving south, no?

Using Booking.com or any website, search for a hotel with parking. If want to stay walking distance from the historical center, select 0 miles from downtown. If you don’t care, since you have a car and you can always drive in, choose any hotel with parking. If you don’t stay within walking distance from the historical center, and want to drive into downtown from the hotel, park near the stadium, parking lots are all around the Fortezza Medicea (Medici Fortress). It’s a quick walk from there to the Piazza del Campo.

It’s up to you where you want to stay, but I like to avoid frequent hotel changes which are wasteful. I thought you had only 2 nights. If you have 3 nights and want to head south, then you can spend one in Siena then 2 in Montepulciano/Pienza, then proceed to Rome. You can return your car in Chiusi, Orvieto (Hertz only), or Rome.

Yes, we have 3 nights - I had planned to spend 2 in Siena and 1 in Montepulciano..then heading to Orvieto to drop the car and pick up the train. Sounds like the opposite may work better - 1 in Siena, 2 in MP, then to Orvieto. Thank you!

Question...how are you getting your luggage from Florence to Siena??

The bike tour operator can put it in the van for us :)

^^^
If it is this bike tour, luggage transport is provided. This sounds like a great way to see the countryside. I see they get you well out of Florence, which will make it a manageable trip. It would be too long to ride from Florence. I'm familiar with that route and you'll go through some lovely country.

Here's the one we are doing:

http://www.ibiketuscany.com/tours/view/florence-to-siena-soft

Oh, ha ha! Yes, the same one, just the shorter version :)

oh, wow I am bookmarking that bike tour site. It looks wonderful! I don't have a new thought on your itinerary, sorry. I'm usually in the camp of stay longer, no one-night stays except the night before departure. But the idling slowly south day by day with a car sounds amazing and relaxing in this case, as you're not racing to catch specific trains and worrying about connections. There are no bad choices here. Please review the bike tour in either a trip report or a review when you get back, I'd love to hear how it went as I plan a 2019 trip to Italy.

Thanks! It has fantastic reviews on TripAdvisor.

And yes, that was my thought - it's only 1 1-night stay, and I feel like it's a stop on a road trip on our way south :) Not stopping to see anything specific, just sort of amble about and eat and drink.

While it is certainly a matter of opinon, I would not equate Florence and Siena. In the case of art, the Renaissance was very late in arriving in Siena, so that's quite different. And the foot tourism experience is very different, with less walking required, once you are up the hill. Siena is far from my favorite art city in Italy, although it is an essential visit. The OP has omitted the month of the trip, which makes a huge difference in heat and crowding. But I would rate Orvieto far above Montepulciano for art and churches (I know nothing about Agriturismos.)

If a bicycle is still involved, the elevation of the sleeping-city might make a big difference. Many hill towns, like Siena and Orvieto are high above their valleys, and (I presume ... ) an exhausting return home on a bike. (You might wish to investigate whether bikes are allowed on elevators and escalators from parking garages below the cities, when available.)

We will be there in late October.

The bicycle is not a factor in the decision. We are doing a 1 day bike tour Florence-Siena and that's it. The tour operator will handle equipment, luggage, etc.

Late October will be a lovely time to visit. It will be cooler but pleasant and not nearly as crowded.

I have been to both Florence and Siena and yes, they are very different, but they or more alike than Florence and Radda or Siena and Montepulciano. They are both fairly large urban cities compared to small hill towns. I offered the suggestion as a possibility to have a larger breadth of experience on a very tight schedule.

Subsequent information shared by BostonTraveler123 makes me feel that both Florence and Siena can be accommodated under the present plan.

If this is your first visit to Tuscany, prepare to fall in love! Also start saving as soon as you get home, because you'll want to return.

Turns out the bike tour arrives in Siena at 1pm! So we'll have the entire afternoon and evening to explore. I may drop one of the nights in Siena then so we can have another night out in Montepulciano instead.

agriturismos in area around Montelpuciano