Help with itinerary needed, so here goes!

Sep and Oct are perfect months to go to IT. Fly into Venice and make sure you take a water bus at twilight from the train station to / from San Marco Square or beyond. Seeing the palace interiors illuminated by the elaborate crystal chandeliers that adorn their spacious foyers will let your mind take you back in time. You won’t see the decay; you’ll see the unique architecture instead. I also like to spend the day getting lost, so I would spend three nights not two so you can slow down and roam the lagoon and get off the beaten path.
You can take a direct train from Venice to Florence (2h 15m) and spend another three nights there. Once you buy your plane tickets and reserve your hotels or Airbnb’s, buy your Uffizi Gallery tickets that sell out at least two months in advance.
I would then take a direct bus to Siena (1h 15m) and make that my home to explore the towns and villages that dot Tuscany and Umbria; at least that’s what I did. You can take a direct train from Siena to Montepulciano (1h 15m), but I would rent a car to see Assisi (2h), Perugia (1h 45m), Pienza (1h 15m), Montalcino (1h) and Cortona (1h 15m). You can then drop the car off at Rome’s airport (2h 45m).
I agree that you can combine some places within a day. Here’s something similar to what I did:
• Siena → Montalcino → Pienza → Siena
• Siena → Assisi → Perugia → Siena

If your home base is in the Tuscany region, you can fly home from Milan. Siena to Florence, and then the train from Florence to Milano Centrale is two hours. I just stayed at the modern MOXY Hotel at the Milan airport the night before I flew home last time.

This trip report covers some of the towns you’re considering. One of the fall festivals in Tuscany is the Luminaria of Sante Croce at Lucca in September. The Arezzo Jousting festival is near where you’re considering, also.

https://community.ricksteves.com/travel-forum/trip-reports/solo-trip-to-italy-2018

There's a nice ceramic museum in Faenza. Faenza's not terribly far from the lovely Ravenna, but it's not particularly close to the places you've mentioned. Although you can get there by rail, you have a lot on your plate already, so it probably doesn't make sense to attempt this unless you decide to rent a car for a few days..

Some towns really are small enough they can be seen in just a few hours. They may be places you go more for the atmosphere than for specific sights. Others (like Orvieto) are larger and have quite a lot attractions worth visiting. Assisi's population is nearly 15 times Pienza's; Siena is more than 25 times as large as Pienza. That's going to make quite a difference, I think.

Whether you can see more than one really small towns each day may depend as much on transportation as it does on your preferred pace of travel. It can be a challenge in Italy to get to two small towns in one day by bus; buses often run very infrequently. I've often had to choose between sitting down to a real lunch and catching a bus that will be the last one for about 4 hours. With a car it is very doable to hit more than one small town a day if the towns aren't too far apart.

We have booked a week in October in Perugia in order to visit Umbria. Prior to that we have two nights in Oriveto. We plan to visit Assisi, Spello, Spoleto, Todi and Gubbio. We plan to take the train or bus.

We spent two nights in Siena and loved it. The other towns you mentions are a bit away from Umbria, but you could pick two cities to base. I suggest Perugia for Umbria.

A couple of thoughts. There is a trade-off to not moving very frequently. That is the time and stress of driving. My rule of thumb is that anywhere more than 1.5 hours away is not a day trip. 2 to 3 hours rt, day after day can be very wearying; and the hilly, winding roads of Tuscany are demanding on the driver. 4 hours rt is out of the question, unless it’s a one off, followed by a couple of days of recuperation.
Since you have already been to Siena, I would find a different base. Perugia? You could then include Gubbio, which is known for ceramics,and, of course Deruta, “ceramics central.” If I recall correctly, there is a ceramics museum there. There are the small, but charming towns of Bevagna, Montefalco, and Spello nearby. All 3 can be combined in a day.
Pienza is tiny, so can easily be combined with another town.

We find we travel much differently in the Summer than in the fall due to the sun setting time. In the Summer we are up later, out and about much later at times being out till midnight and not even noticing. The Summer is a more leisurely pace knowing we are not chasing the daylight. In the fall we are up and out the door early, hitting the ground running, still having a late dinner but then heading back to our lodging earlier. Summer is HOT and sticky which can drain us, the fall is perfect for us. Plus I have a paid holiday in September and October that I take advantage of and always work one of those days into my time off. I love a good walking food tour, look into that in Florence and Venice.

I have tried to reply twice and it disappears. Thank you for all of your suggestions and I will definitely consider them. Jean, your travel notes are wonderful. Bravo to you for flying solo successfully. I like the idea of a home base other than Florence. I considered returning to Cinque Terra, but if we don’t hike I’m not sure it is a wise use of those days and travel time. And some hill towns would need to be eliminated. Do you agree or not?
I am willing to eliminate some towns if it makes sense to spend time in one town for 2 days to get a better sense of life there. I know we can bus to Siena from Florence. Is driving the only option to visit the other towns?
Any favorite wine tasting places? Cooking classes? I took one in Assisi and loved it. Can we go to see how grapes are harvested and prepared for wine? Or olives? I’m being romantic I know.
How is Perugia different from Assisi?
My brain is full, yet happy.

Did you find the shorter days affected your trip in any negative ways?

I believe all the places you mentioned have bus service. Some also have train service. The issue is that bus service may be impractically frequent for the small places like Pienza, Montalcino and Montepulciano. They're quite close to each other, but each is at least 2 hours by bus from Siena, and to link two or more of them together, you'd need bus service running at the right times of the day. It would be a slog, and you might well end up with a lunch of packaged peanuts.

You can start exploring the logistics on the website Rome2Rio.com. Unfortunately, you cannot trust the travel times, frequencies or fares displayed by Rome2Rio. Even before the pandemic they were often wildly off base. But if you keep drilling down you'll find the name of the company providing the bus service and usually also a link to its website. In normal times you'd be able to find schedules on the company websites. I don't know how accurate those are at this moment.

For rail timetables go straight to the source at trenitalia.com. You'll have to use the Italian spellings of city names, so Firenze for Florence. Florence has multiple train stations, but you don't have to figure out which one is used for which destination. Just choose Firenze (Tutte le Stazioni).

Cortona's not too bad a train ride from Florence if you want to make it a day-trip (and it doesn't need an overnight), but trains don't go to hill towns, so you have to make the last leg of the trip by bus or taxi.

Perugia and Assisi are day-trippable from each other, but I wouldn't want to day-trip to either one from Florence or Siena. Certainly handling both the cities that way would be a bad plan (over 8 hours back and forth over two days). Using public transportation to switch your base to one of those cities for a few days wouldn't be a problem. Perugia is easier to reach from Siena (probably best by bus) or Florence (probably best by train), so I'd make it my base and day-trip to Assisi.

Most travelers who opt not to sleep in both Florence and Siena choose to use take a bus between the two because the bus drops them off much closer to the historic center.

In short: If you want to see all the places on your list, I think you're going to need a car. If you're willing to pick and choose (perhaps partly on the basis of the transportation schedules), you can stick to trains and buses. I suppose there's a possibility you might find a one-day bus tour from Florence or Siena that would get you to two of Pienza, Montalcino and Montepulciano. I know I've seen bus tours in the past that combined San Gimignano and Volterra.

We’ve been to Tuscany and Umbria twice. We’ve based in Assissi (my all time favorite town in Italy) and toured from there for several days by rental car, then based in Siena (my least favorite) and toured from there for several days.
Montalcino, Montepulciano, Pienza and San Gimignano are wonderful.

2 days (nights?) in a town is only a day and a half
Give Venice 3 and you won’t regret it
Take vaporetto out to Burano

I believe toursbyroberto does a trip from Siena that will get you to Pienza, Montepulciano, another town? and possibly a winery stop
Otherwise you’ll want a car

If you take a day trip from Siena give Siena 3 nights if you really want to immerse in daily life

I imagine we will be renting a car to reach the towns more easily and that is fine. I like your ideas about having 2 bases to minimize daily driving time in Tuscany. I’m still on the fence about returning to Assisi. While beautiful, I’m trying to decide if there is enough there, other than the obvious spiritual locations I have already visited.

Some things are starting to fall into place thanks to all of you. I’m sure I will be back with more questions at a later time!

Gosh, where to start! Okay, the season. Yes, September, especially after the 15th when kids are back in school, is a perfect time to be in Italy. That is now our preferred time to be there. The heat is going away, the sea is still warm, and the tourist spots are getting quieter. Another poster mentioned staying in one place for a bit at a time. I agree, even though I love to drive. It is nice to settle in and really know a place. It is probably best to pick a region, or to really immerse into the larger cities. Also, don't be afraid to cross the border. If you are in Venice, it is really a shame not to visit the Veneto back country and Treviso, or even to get up to the Dolomites around Corvara in Badia and Cortina. Trieste also has it's charms, and the part of Croatia that is nearby (Istria) is beautiful. Slovenia too!!

It is also a shame not to use a car to get around. You have so much more access to the countryside and towns that way. The trick is to set things up so you avoid having the car in a major city, which is a hassle to be avoided. For example, you might rent a car from Marco Polo Airport in Venice, and drive around the region. You then renturn the car and take the vaporetto or the Alilaguna into Venice at the very end of your trip. Or you do it in reverse, or bookend with, say, Verona or Milan, returing the car to that city's airport. We frequently rent cars in Venice and then drop them off at Ciampino (Roma), spend a few days in Rome, then catch our plane stateside from Fiumicino (Leonardo Da Vinci).

Personally, we love Venice and its charms. It is much less crowded now that the cruise ships have been moved further away, and the neat thing about Venice is that it gets really quiet as soon as you walk 20mn in any direction away from St. Marks. The Giudecca, Arsenale, Lido, and Dorsoduro each have their charms and are all walkable 100%.

We also love most of Italy, but in particular the Lakes District (Como, Maggiore, etc), the Amalfi Coast, the Cinque Terre, and southern italy is amazing as well (Matera, Alborobello (Puglia), Lecce, Monopoli, the Gargano, etc.).

And then there is Sicily. Just beautiful. And perfect through October. The only issue with Sicily, is getting there this year, as I am not sure that Easyjet etc. have firm flight schedules. Major carriers into major cities may be OK, but I would expect the budget airlines to be chaotic for a while.

If you must take trains, allow lots of extra time for connections, as trains frequently do not run on time in Italy, and that was before Covid. It is not as bad as the UK, but it is not France or Germany. And be especially careful in stations, and even more so as 2 women travelling. You will get a lot of unwanted attention in these types of places, and you will be a target of pickpockets and Malvolenti.

Possumracing47.....Hmm, so many great suggestions from north to south. Maybe I should spend a whole season in Italy, right? Thanks.
For those of you that travelled in fall with the shorter days, what did your evenings look like, besides dinner?

Can you please give me your opinions on visiting the Le Marche area with this Italy Undiscovered 7 day tour? Itinerary offers things we are interested in, but I’m unfamiliar with the area. Is it too pricey? We could also go to Florence before or after for 3 days.

https://www.theitalianontour.com/project/7-day-italy-itinerary-le-marche-abruzzo-2022/

Thank you.

Can you please give me your opinions on visiting the Le Marche area
with this Italy Undiscovered 7 day tour? Itinerary offers things we
are interested in, but I’m unfamiliar with the area. Is it too pricey?
We could also go to Florence before or after for 3 days.

https://www.theitalianontour.com/project/7-day-italy-itinerary-le-marche-abruzzo-2022/

People go on tours for many different reasons, but I don't think a tour is necessary for the Marche region, and I had trouble figuring out the details from that website. If you can drive a car, you can do anything.

In my opinion, that tour is rather pricey. Day 7 isn’t really a tour day, and day 1 is dinner and bed. Therefore, you are paying $3700 for 5 days and a bit. You won’t see some of Le Marche’s outstanding sights; e.g., Urbino or the Frasassi caves.

I do acknowledge that the social side of being on a tour can be a plus. In our 3 tour experiences during over 35 years of European travel, we have enjoyed the company of our fellow travelers. However, you do have to hope that everyone in your group will be compatible.
If you are staying in Umbria and have a car, it’s quite easy to get to LeMarche for a few days.

Yes, I felt it was expensive for really just 6 days. I’m not normally a tour person, but was open to considering it. We will just plan our own trip which I’m sure will be wonderful. Thanks for your advice.

I just noticed Gubbio is on your list. The drive from there to Urbino takes less than 2 hours. That would be a place to slot in 3 or 4 days in Le Marche. The Palazzo Ducale in Urbino houses a fine art collection, with several works by.

We stay at Villa Trasimeno in Umbria. The owner is a chef and has a package that includes a room, breakfast and dinner, daily sightseeing and either pickup or drop off in Rome or Florence. We went to Assisi, Montefalco, Deruta, Montalcino, Montepulciano, Siena, Orvieto, San Gmignano with him. The only problem is that you have to pay cash so a few trips to the ATM are required.

http://www.villatrasimeno.com/