Florence, Siena, Orvieto & Assisi?

Just outside of Venice is the lovely little town of Treviso with some nice restaurants - it was such a breath of fresh air compared to Venice. Maybe 20 minutes from the canals.

You can easily take a train to Sienna. Sienna is somewhat large. Like most of these places, if you get a hotel with a parking lot, you might be on the outskirts of the city. We stayed at place in Sienna where we needed to take a little shuttle bus to get up to the actual city. So it might be better to go by train then pick up the car there.

Assisi and Orvieto are more of car destinations. I was very charmed with Orvieto, but not so much Assisi. There is a nice view from the plains looking up at the city, but the city itself is so-so, although there are the remnants of a castle just to the side of it. There are many other car destinations which are pretty nice - San Gnimango, Voltera, Montepulciano, Cortona.

Forgive me if it sounds like a silly question but are you SURE your cruise ends in Venice? Many of the larger ships have been moved to ports elsewhere, and it has come as a surprise to some cruisers that their "Venice" port was actually Ravenna, Trieste or some other more distant location. thus the question. :O)

Personally it is too fast for my liking. We recently had two nights in Orvieto and Siena and enjoyed our full day in each of them. Orvieto in particular was lovely and peaceful. ( We had just come from Rome).

I've not been to Assisi, but if you drop that and give Siena two nights, I think it would feel more relaxed. What about taking a long travel day straight to Siena first, then have 3 nights at the end for Florence?

Siena 2 nights
Orvieto 1 night
Florence 3 nights

If you stay in the town itself, you could even avoid picking up a car, as you can easily bus or train from Florence to Siena and to Orvieto

Kathy, thanks for double checking! We are ending our cruise in Fusina/Venice. :-)

I hate 1 night stays although with a car it’s not as bad

I think I’d go right to Siena-2 nights
Then choose either Orvieto or Assisi-2 nights
Then Florence 2 nights

If you pick up car as you leaveSiena -Hertz- you can drop in Orvieto and train back to Florence
That allows you to drive the beautiful Val d’Orcia

As I recall the drive from Montepulciano to Assisi wasn’t all that interesting

We’ve enjoyed 2 nights in both Orvieto and Assisi

If you opt for public transportation to Siena: The usual recommendation is for the bus, rather than the train, from Florence. The bus station gets you much closer to the historic center. However, if you're already coming in on a train from Venice, I don't know that it's worth the hassle of switching modes of transportation in Florence.

The basilica in Assisi is magnificent. I also loved the very untouristy (as of 2015) upper town. The streets right near the basilica were chock-a-block with tacky shops selling cheap religious souvenirs. I urge you to head uphill on the bus and walk downhill through the Middle Ages. I didn't have a car in Assisi, but I noticed large escalators to help visitors move from the parking lot(s) to the basilica.

I also loved Orvieto, which has a really impressive number of worthwhile sights for a hill town of less than 21,000 people.

I think it would be easier to do a good job of seeing Assisi in one day; plenty of people treat Orvieto as a day-trip from Rome, but I think it's more than a one-day destination.

Unless you're a religious pilgrim, I would go to Orvieto instead of Assisi. When my husband saw my pictures of the cathedral in Orvieto, he said "Wow".

Car rental in Florence-arriving by train, the car rental street Ognissanti is walking distance unless you have lots of or heavy, large suitcases. Driving out of the car rental garage there is no worry about getting caught up in the ZTL. It is a one way street where after about a block you turn left at a roundabout and follow that road out of the city. Very straightforward, very easy. Plus, the rental agencies are used to giving these directions as the ZTL is of such concern.
Somewhere in the Italy forum Roberto da Firenze has given explicit directions. Worth a search.

Even if you stay, take a cab to the rental agency and get your car. Far easier than the airport.

Orvieto is quite lovely. We rented a wonderful ground floor apartment just off the main square. The cathedral was a "wow", and the underground tunnel tour was interesting. I would definitely include it as Christine suggested in her itinerary.

Thanks to JR, here is the link to Roberto da Firenze’s info

https://community.ricksteves.com/travel-forum/italy/car-rental-in-florence-airport-vs-train-station

I'm never wild about having a car in Italy - that's just me (and maybe some others). That said, trains and buses will easily get you where you want to go and you'll be able to enjoy the views rather than fear the traffic. And, I think you'll be short-changing each of those cities. I think I would cut the night at Antica Olivaia. Siena is marvelous and far more than just the Duomo. It's an easy bus ride from Florence (about 90 minutes) through some scenic areas. Orvieto, for me, was not disappointing but the highlights were the spectacular views as you walk around the rim of the plateau and, of course, the terrific Orvieto Classico white wine. Assisi has a big place in my heart. It is filled with history, art, lovely walks and 'peace.' Stay on the middle level where Piazza Comune is. There are some very nice hotels and restaurants there. The area closer to Basilica San Francesco is much more touristy and crowded. At night the Piazza Comune is a very relaxing place to just 'be'.
Flying out of Rome? I always find that easier (but I'm flying nonstop to Philadelphia) but you really do need to not worry about getting to the airport (train or taxi from Rome are easy and affordable).

All that said, any chance you could prolong you stay several days so that each city gets more (deserved) time?