NO CAR, MID-DEC: Agriturismo/Villa/B&B in the Tuscany or Umbria countryside please?

With no car in mid-December, I would opt for a small town rather than an agriturismo. Living in the countryside without a vehicle is not really part of the local lifestyle, if you plan to visit places off the property.

Perhaps others can help you, but off-season, I would prefer a small city.

Tuscany is a place best traveled to via auto. The really good hilltowns are often not accessible by train. Buses can get you to most popular destinations, however buses would limit seeing too many places.
I would suggest you visit Orvieto, a very popular hilltown 70 minutes north of Rome Termini by train. There are a number of good B&B's and hotels there. You could do some day trips by bus out of there, including Civita.
Florence is another place you can use as a central location to do day trips out of. It's not the countryside, but buses are easily accessible and many tours of Tuscany start there.
When I was staying in Tuscany and Umbria, I found accommodations on Booking.com. You can filter any search by low-high prices and see what's in your price range. We found many accommodations in the countryside for 70 Euros generally, however larger cities may be a little higher in price.

Please check a map. The proper sequence, south to north, is Amalfi, Naples, Rome, Florence (Tuscany), Bologna, Venice, Milan.
You are talking about budget constraints, but back tracking back and forth is going to cost you a fortune in train fares. High speed trains aren't cheap.
If you go in December, I would strongly recommend you don't stay in isolated villas or Agriturismo, those are hard to reach in summer let alone winter.
If you don't like big cities, you can stay in smaller cities or towns. Along the Rome to Florence rail line there is Orvieto, Cortona, and Arezzo. Find accommodations there. Also Florence doesn't have a large city feeling inside the historical center.

Must disagree with David that the "really good" hill towns are inaccessible by public transportation. True, you may need to take a local bus or taxi from a train station into town, but buses are often timed to coincide with train arrivals. You will have dozens of choices with good rail or bus links to other towns. Look at Anghiari, for example. Arezzo is bigger, also a good choice. In winter, you may prefer someplace that has a bit of evening activity, like a small town, since the daylight hours will be shorter.

Orvieto is a good choice for Umbria, so is Spello, near Assisi. Or Assisi itself.

I am glad Zoe mentioned Spello. It is a very charming small town. We stayed there one December and used the train and bus to go to other Umbrian towns. The train station is a 20-minute walk from the main square. We did not find that unpleasant, but there is also a taxi that meets every train.

Everyone, thank your for enlightening me and providing some suggestions, I truly appreciate it.

I am actually considering staying in an apartment/B&B in a small town, and given the number of beautiful villages and towns from south to north, I am sure there won't be a shortage of good choices.

What I was hoping for were personal recommendations for accommodations that are slightly out of town as I wouldn't always want to be out touring. I'm only budgeting 3 nights in the area and I'm looking at my stay as a way to recharge in the middle of a hectic holiday. I might even get some writing done. But I'm now better informed that it's impractical to want to isolate myself when a small town/village would be more interesting. Thank you.

Roberto, in my months of browsing the RS forums, I've always considered your answers helpful and I'm glad you replied. Please hold on to your keyboard as what I will say might shock you off your seat: I actually HAVE a map. I even look at it occasionally. Believe me, your suggestion is how I'd originally planned to travel, but my reasons for the haphazard routing are more about timing than anything else.

As I mentioned in my original question, my weird route should be made as another post, but I'd like to present to you my problem anyway and hopefully get a better route suggestion from you.

The places I WANT to visit are: Naples (actually more like a day trip for the food and not the sights), the Amalfi coast, Tuscany, Florence, Bologna, Venice, and, finally, I will end my trip in Milan.

My travel dates are December 13 onwards, and I need to be in Milan by the 27th of December (as I have family there). I am spending 3-4 nights in the Amalfi coast, then another 2-3 nights in Tuscany/Umbria/one of those charming towns I was hoping to get a recommendation on, then maybe 2 nights in Bologna, 3-4 nights in Venice, and I want to spend Christmas in Florence (although I have also begun researching Christmas in Venice).

How can I hit the places I want to go and still spend Christmas in Florence? Thank you, and I hope you can help un-crazy my crazy plan!

PS: I'm visiting Italy more for the food than the sights and culture, but I'm not so boorish as to completely ignore historical sites and masterpieces. Because of my limited time, I had to choose to eliminate Rome from my travel plans. Maybe when I meet up with my family members, we will have enough time to visit Rome.

Where are you flying to?
I presume you are returning from Milan, so I'll presume that you are flying into Rome (Naples also is a possibility but with fewer flight options).
I assume you arrive on Dec 14? So you would have 13 nights on the ground before you need to be in Milan on 12/27.
So, this would be my plan:
Upon arrival, on the same day, go immediately to Naples area (Sorrento/Amalfi Coast) by train.
Sorrento/Amalfi Coast: 3 nights (I recommend you stay Sorrento, a bit larger, more accessible, and with more options. Amalfi coast is accessible by bus from Sorrento)
train to Tuscany
Tuscany smaller city/town: 3 nights (I recommend the cities of Arezzo or Siena, small enough, but with some life in winter).
Florence: 2 to 4 nights
Bologna: 0 to 2 nights (you could even commute from Florence, it's only 37 min by high speed train)
Venice: 3 nights (spend Christmas in Venice)
Total above 13 nights (just adjust Florence and Bologna nights as you see fit). After which, on the 27th of Dec. you go from Venice to Milan for the remainder of your trip with your family.

I spent lots of Christmas days in Florence. Although lively in the days preceding the 25th of Dec. however Xmas day itself is a day when most Italians spend time at home with their family stuffing their faces until they are about to explode. People start coming out later in the afternoon (those who can get off the table and walk without collapsing on the floor from the huge amount of food they ingested), for a stroll downtown doing some window shopping or to the movies (most if not all stores will be closed). Venice is probably not much different, but at least it's a bit unique.
Make sure you are not planning to travel on buses on Sunday and especially on Christmas day. Buses will be nearly non existent on Sunday or holidays. Trains should be largely available (on a more limited schedule).

In December 2015, I spent a lovely week in Cortona. It might fit your needs if you choose to stay in a town. For such a small town, there are quite a few exceptional restaurants. I took several walks "in the country" by visiting Le Celle and following the old town walls on a loop of the town.

Additionally, a few summers ago I stayed at Hotel Porta Romana (recommended in Italy) near the Porta Romana City Gate in Siena. It might fit the bill for your desire to stay outside a city without a car. While it is within an easy walk to the city, it truly feels and looks like it is in the country.

Good luck and enjoy Italy!

Sharon

Sharon, thank you for suggesting Cortona! I'd been considering it but was reading mixed reviews about it. I shall reconsider.

Roberto, regarding Christmas in Florence, I actually mean the days leading up to the 25th as well, not just Christmas day itself.

I am actually flying from Lyon on the 13th itself and landing in Naples.

Back to Florence, I just feel that I want to spend more days there given the number of things to see and do (including spending pre-Christmas there) than Venice.

I hope you don't think I'm being stubborn. I want to be reasonable about this, and I WILL research Christmas in Venice.

I just hope there was a way to do Christmas in Florence. Sigh.

Anyway, if you have more suggestions for small towns/villages to experience, please feel free. I have decided to stay in a town instead of an isolated place that's hard to reach, so thanks for helping me make that decision.

Just stay in Florence 5 nights and go to Venice, on the afternoon of the 25th and spend just 2 nights there (25 and 26) before heading to Milan on the 27.

Having lived in Italy (Florence) most of my life, and also spent some Xmases visiting from the US, I can tell you that Xmas day itself is not that exciting anywhere. The days leading to it, especially the weekend before up to the 24th evening, maybe yes, but Xmas day is a rather ordinary day when people stay home with family and have a huge Xmas luncheon which lasts hours. Most if not all stores will be closed too, so all you can do is window shopping in the city center. Museums are closed as well. The only things open are some bars/cafes/restaurants and movie theaters (going to the movies on Xmas day is a popular activity) and of course going to church in the mornings. I would actually consider using Xmas day to transfer from Florence to Venice. Morning in Florence at the Duomo, then train to Venice, and spend afternoon and evening in Venice. Trains run on Xmas day.

Once again, Roberto is giving you excellent advice. I strongly encourage you to take it.

Happy travels.

Happy travels!

Roberto has given you good advice. You could also check in the small town of Greve, about 18km south of Florence. Last December we stayed at Castillo di Verrazzano. I don't think it would work for you because it's a pretty steep walk up a hillside to get to it. There are some hotels in town that fit your budget. Check them out.

Greve is on a major bus route to Florence, so getting there and back would be easy. It's a quiet little town. There are also other towns on the bus route that you could explore.

We had good weather while we were there. There were a couple of mornings with frost, but it warmed up nicely during the day. We normally wore a light jacket or just shirtsleeves.

Thank you, DougMac for mentioning Greve. I'll have to add it to my list of small towns to research.

Roberto, I like that suggestion better. I'm not so hardcore set on spending the 25th in Florence. I'm more interested in the days leading up to Christmas. Then I'll move on to Venice.

Thank you!