scenic bus/train trips in Umbria and Tuscany

We toured Tuscany and Umbria last year for 2 weeks while on an anniversary trip. If your intention is to see the countryside versus just connecting some of the major towns then a car really is the way to go. I too was initially a little hesitant to rent one but after familiarizing myself with all of the cautions and rules of the road as mentioned here by other posters I really am glad we opted for the car. We found that driving in rural Tuscany and Umbria was a joy - the freedom to go wherever we wanted and stay as long as the spirit moved us made the trip quite enjoyable. It does require some advance homework in order to sort out things like the ZTL's and parking in some of the hilltop villages, but with a bit of advance preparation it's really no big deal.
Aside from the ease of movement that having a car provides, it might be the better option versus public transportation if you want to continue to avoid crowded spaces and to practice at least a modicum of social distancing in the (hopefully) post Covid era.

For a unique experience, though expensive, this might fit your expections.

https://www.thelocal.it/20190208/weekend-wanderlust-siena-and-a-steam-train-ride-through-wine-country

Busfox also connects many smaller towns, but you need to check carefully the return times.

Trenitalia has a line that connects Siena with Chiusi and intermediate stops along the way.

https://www.lefrecce.it/msite/?lang=#search?noOfAdults=1&ynFlexibleDates=off&arrivalStation=Chiusi-Chianciano%20Terme&selectedTrainClassification=2&tripType=on&selectedTrainType=regionali&departureStation=Siena&parameter=initBaseSearch%E3%80%88=en&departureTime=07&departureDate=21-09-2020&noOfChildren=0

Click on info then more details.

As far as the best utilization on time. The ability to visit more than one town/village a day a car can't be beat. Just be sure you are aware of the rules of the road for Italy.

https://en.wikipedia.org/wiki/Ferrovia_Centrale_Umbra

Here is some info about another smaller train service from Perugia in Umbria that serves small towns that Trenitalia does not.
I don't have any current info about it, but maybe someone else here does?

We have always rented cars in Tuscany and Umbria and can’t imagine using public transportation in this part of the world. You would get a surface experience at best if you don’t drive around these regions. We love driving through vineyards and visiting very small towns.
On one trip we spent two weeks in Spello, Umbria which has a train station. We never saw one train come or go although they are supposed to have train service.
I highly recommend renting from AutoEurope.com in Portland, ME, a broker., especially for Italy. They will stand behind you if you have any problems.

I think you may misunderstand the nature of the transit infrastructure in Tuscany and Umbria. It's not like training from Hamburg to Berlin. I'm a big fan of trains, but your experience will be best with a car for those destinations. Summer can be very hot and crowded, but the whole post-Covid travel situation is unknown for now. Because we were there in high season, we had to search for parking spaces, and still faced a half-hourly shuttle bus (or a stiff uphill walk) in high-traffic towns like San Gimigniano. I'm not saying that you must see SG, but frescoes and architecture do not travel (!)

There certainly are places with a high payoff for an overnight stay, like Orvieto and Siena. Some posters here have recommended staying in Florence. But I can't imagine being a slave to intercity bus schedules to tiny destinations.

That said, driving in Italy has many annoyances, principally ZTLs and insurance costs.

I have toured Tuscany and Umbria 3 times by different modes of transportation. They included bus/train, rental car and a Tour group. The rental car was best for exploring the back roads. You can stop for a picnic, get lost in very small towns and visit in the local bar or coffee shop and tour unusual places. To do this type of exploring you have to get a variety of tour books in addition to RS books (which just don’t cover these small areas). We also picked up maps covering the two ‘states. The maps are big and very detailed which allows you to pick your own back roads. Be very careful to stay out of restricted driving zones in the cities. They are a big money maker and easy to cross into. My tour was very good covering areas not seen before. There is so much to do in this area of Italy. The people are so friendly in the untouristed areas down the back roads.

Oh, we road the above mentioned Train natura about 15 years ago out of Sienna. It was a much more modest ride and everyone spoke Italian. It was an simple adventure through the countryside. Our train wasn’t a steam engine so no smoke problems.

I am not disagreeing about the benefits of a car, but public transportation also has possibilities. About a decade ago, I traveled by train from Rome to Orvietto, to Perugia, to Cortona, to Siena and then on to Cinqua Terre. The train schedules and transfers were pretty easy, none of the trips were especially long. I would say the scenery was nice but not so wonderful as to choose the train for the views. I did a day trip by bus from Perugia to Gubbio that was more of a very windy, hilly and scenic country roads experience. From Perugia, day trips by train or bus to Spello and Assisi are also easy.

Spello does have train service. We stayed there for a week and easily visited other places by train. That said, we also rented a car for four days once while staying in Montepulciano, because we had learned on a previous trip that we were limited in what we could do by public transportation. We picked up and returned our car in Chiusi. Getting in and out of old town Montepulciano was somewhat challenging, but we had no accidents or damage to the car! This is the only time we rented a car in 19 trips to Europe. On a trip of length you're considering, I'd be inclined to skip the car rental. So you can only visit one town per day from your base. You have time, and the luxury of not needing to race from one town to another. Happy planning!

To add to my above post, info on Busfox and Termme Spa busses.

https://sienavisitor.org/tag/siena-bus-schedule/

Check Amazon or you favorite book store--there are several books devoted to scenic drives in those regions.

If you decide to drive and would rather not deal with the hassle of renting in Florence, consider collecting and dropping off your vehicle in one of the smaller towns (Siena, Chiusi, or Assisi) - any of which is an easy train ride from Florence. That said, there are a few rental car locations on the outskirts of Florence that make getting on your way a pretty straightforward process. Starting your journey along the SR222 route ( heading south via the Chiantigiana ) would be a great way to begin your driving adventure.
Per Suki , booking thru AutoEurope is recommended. Their prices are competitive and they spell out the insurance options clearly - not always the norm when dealing with some of the other company booking engines.
Aside from the RS guide, the best publication we’ve found for scenic drives is “Backroads Northern Italy” from DK publishing. You can usually find used copies on Amazon for just a few dollars. It’s a treasure trove of off the beaten path destinations and roads less traveled if you’re interested in that sort of thing.

IMHO the most scenic railway trip is the high speed train between Rome and Florence. The zone between Orvieto and Rome is only sparsely settled and the train gliding through the hills in my opinion is fascinating. - There are a few country railway lines that may interest the railway enthusiast - say Pistoia to Porretta, once the main line between north and south Italy, built to 1880 alpine railway standards, or lines south of Siena; but they are more interesting to the railway buff that any use to the ordinary traveller, as their stations are mostly very distant from towns and scarcely practical.

I researched taking the train and using Perugia as our base to visit Umbria. We plan to spend a week there next October.

The two reasons not to rent a car are FIRST- parking, you many be limited to where you can park near the town centers.
SECOND- peruse these boards that are filled with drivers that received outrageous tickets driving in Italy.

I lived in Europe in the late 80s early 90s and drove in Italy, the tolls on the autostradas are very expensive, also fuel is very expensive. The rail system is excellent.

For Tuscany, you can take the train, do a day trip to Sienna, another trip to Pisa and Lucca (might need to spend the night in Lucca).

Thanks to everyone for the responses and ideas. I'll have to figure out more what exactly I want to see as well as my wife and daughter. One thing I noticed is that car rental prices are much cheaper if you rent a few months ahead. Not sure if this is because I was randomly checking dates in October and thats getting out of high season, or if its always much cheaper if you rent months ahead.
And I do like the idea of renting a car outside of a central city area like Florence. The idea of starting a driving experience in a foreign country in a city with all of its driving challenges is a little scary.

"The idea of starting a driving experience in a foreign country in a city with all of its driving challenges is a little scary."
I felt much the same last year and so can sympathize with your unease at the prospect of driving in Italy. I would only say from personal experience that the terrors of driving there are vastly overstated (at least in my opinion). As I mentioned before, we found that driving around rural Tuscany & Umbria was an absolute pleasure, but then I had done a lot of advance preparation before setting out which greatly lowered my pulse rate and generally reduced any stress I felt initially ... mainly due to some of the horror stories I'd heard from others here about their run-ins with various aspects of driving in Italy. I previewed our routes each day by making good use of the google map app on my smart phone to ensure I knew exactly where the ZTL's were located as well as sorting out the parking - which turned out to be a lot easier that I expected. Fact is that after the first day I was zipping along the rural roads like a local, while being extra careful to be alert for changes in the speed limits, etc.
One particularly easy way to transition into this would be to take the train or bus down to Siena and then collect your car there. AutoEurope shows several options near the train station, one of which is a Hertz location just a couple of blocks down the street. While we didn't rent there ourselves (picked ours up in Pisa) I did walk down there to familiarize myself with the location for future reference. It's just off the SR2 route heading out of town - in fact it's a straight shot from there down to the scenic roads of the Val D'Orcia less than an hour away. Really couldn't be easier. Might also mention that there's parking in an underground lot at the train station - was alerted to it by another poster here and it turned out to be a terrific option - never had an issue finding an empty spot during a 5 day stay in the city and at 2 Euros per day it's probably the best bargain in all of Tuscany.
Motoring around the Tuscan and Umbrian countryside is truly one of the world's great scenic drives. Rent a car - you won't regret it.