Critique this itinerary for a 2-month spring trip

Did AI give you the train info? That’s what I would focus on first. Many of us do come here for the human connection so yes you will get some pushback on the AI.
As for the list, it looks fine but you probably don’t need to stay in both Ostuni and Monopoli as they are so close together.
After getting the transport connections sorted, I would research the day trips you can do by public transport in each place, whether by AI or the old fashioned way (the internet, lol).

What the heck, why not? It'll make for an interesting travelogue story and you are traveling in such a way that you really can be flexible. If you're bored, move along. if you love a city, stay. I'm jealous. And as a destination, Chioggia absolute cannot be beet.

That pun made my day

I've removed other posts to give the official take. Yes, this forum is intended to be human in its interactions. Per our guidelines...

"Creating posts with automated technologies such as bots, ChatGPT, or other forms of AI are prohibited. Suspected or confirmed use of such technologies can lead to an immediate ban."

In the interest of kindness to the OP, I'll let it pass this time since most of the post is human written and it's just a list, but it won't pass in the future. Thanks for avoiding use of AI here in future posts.

Organizing a complicated itinerary is basically the Traveling Salesman problem, which gets more challenging the more stops you add. I was curious to see how an agent would perform compared to a human (me). But I'm happy to edit out the author of my intinerary if it will put me in better aroma with the forum. I'm here for the value judgements that forum folks are so good at: is 9 nights in Cortana too many? Would I better off splitting that time between two towns, and if so, which ones? And so on.
@Chris, I wondered about Ostuni & Monopoli - do you prefer one over the other? I'd knocked Matera out of the running because I'm averse to driving, but maybe that was hasty. Glad to hear you approve Chioggia ;-) It's been on my wish list a long time.

I actually was thinking that 9 nights is a lot for Cortona. On what basis did AI allocate number of nights? It is not clear to me whether this is mainly a challenge/exercise to play with AI or if you are seriously asking for travel advice. (I don't necessarily object to the challenge/exercise but would prefer to know). For actual. travel, key questions would be whether you are looking to do day trips and if so, are there places nearby and accessible without a car (your stated preference, I believe) that you would want to visit?

I have only been to three towns on your AI list: Gubbio, Orvieto, and Cortona. I thought they were each wonderful. However, there is no train in Gubbio.

My other comment is, would you really want to stay in that many walled cities, one after the other, and make that many moves? When I did a trip to the Netherlands and Belgium, at some point I realized that I had visited 6 or 7 canal-based cities in a row and that I although I liked each one, I might have preferred more diversity of scenery interspersed. But that might just be me.

It really depends on what you want to do in and around those towns (and without a car), and you didn't mention what your interests are. For me, I would want more variety. Discount all of the following if you've made long trips like this previously, and this number of days in each town is suitable to you.

My spouse and I are semi-retired (I can work remotely), and have been taking one-month trips to Europe twice a year for the past several years. We quickly realized that one month away is the right amount of time for us; we start missing our pets, our home, and what we do for fun at home by the end of that time. While we are definitely spending more time in most locations than we used to, I also (more than my spouse) realized that I need more variety, some time in big cities and in rural areas, and more variety in terms of activities. While I love sitting at cafes and people-watching, I get bored after a while. I recognize that all this is partly a "me" issue, that others don't have. (If you have any suggestions on this, let me know!)

Our least-wonderful trip was to northern Italy, in areas that I do love. But on this trip, in analyzing it afterwards, we spent too much time in towns that were similar sizes (though not all walled), even though our time was in Emilia-Romagna, Tuscany, and the Piedmont. And, out of our control, the weather was not great (sometimes that happens), and lots of rain and fog in small towns doesn't provide a huge amount of options of things to do.

I will add that I really enjoyed Urbino, but we did driving day trips from there in addition to spending time in Urbino (many interesting places in Urbino, and not so many tourists, which was nice). And Venice, of course. You could spend more nights in Venice, but you've been there before.

On the AI front, I once experimented and entered a query asking for an itinerary for someone who wants to visit, then listed five specific wants. The response I got was something I could have pulled off any website, any guidebook, and didn't include anything that I hadn't already heard of or considered. So, it didn't work for me.

@CDinDC seriously looking for advice. I'm all about about the day trips, and will rent a car if necessary/worth the trouble. But if I can skip it? Gravy. It's true that Gubbio has no train, but the bus trip sounds easy enough, and the Easter festivities reminiscent of southern Spain. Would we get tired of walled cities? Maybe. The front end in Puglia is a very different landscape; perhaps I should look at shifting a week from the north to the south?

@Lexma we've made a fair number of longish trips, ranging from two months in Venice, to two months in 10 countries/15 cities. Both extremes were enjoyable, but the two months in Venice, with day trips every weekend - that's the adventure I revisit in my mind. The day-to-day routines of life in Italy are a welcome change from my daily rounds at home. Our travel routine is: daytrip and wander around in the morning; get lunch and shop (market/vino sfuso/Gaspar). Work in the afternoon. Go out in the evening for passeggiata, cicchetti/tapas, sometimes dinner. Towns that accommodate this pattern have worked well for us, and I'd love to find more of them.

That is a lot of days in each of the towns. I have been to about half the those on your list.
If you visit Umbria (you list three cities from Umbria) be sure to visit Spoleto, Assisi and Perugia.
https://www.italyreview.com/top-10-places-to-visit-in-umbria.html

Also, we loved Siena in Tuscany.

I would have zero qualms about week plus stays in any Italian city. I’ve never run out of things to do anywhere, and I’d rather have some calm days versus packing up and moving excessively.
It all comes down to the things you want to see and do.
Things I’d still be drilling down in are the travel between cities, as some appear long (I have not mapped any of this). Like Monopoli to Gubbio for example. Maybe there are some more stops to be inserted for a bit more variety, perhaps another Marche stop?

@valadelphia I too am suspicious of several of these proposed transfers, the Puglia-to-Gubbio one especially (Rome2Rio claims it can be done in about six hours, routing through Ancona). Add a stop, balancing the annoyance of a long travel day against the PITA of "moving house?" Maybe Pescara, Termoli, or Senigallia?

Senigallia is fantastic!
Be sure to verify RomeroRio results. they can be wonky.

Rome2Rio is so unreliable as to be nearly worthless, as far as I'm concerned. There's no reason to use it unless you can't get where you're going totally by train, and even then, its bus information is dicey. You simply cannot trust its travel times, frequencies or fares.

I regularly spend 4 months at a time in Europe, using only public transportation, and I am a slow traveler. Although I like visiting small towns, my preference for stays of more than, say, 3 nights is for bases that aren't tiny, because I'm likely to have better transportation options there. In addition, they're likely to have enough local sightseeing that I don't need to take so may day trips to fill my time.

In addition, I really don't like the idea of having to start a bunch of day-trips with a bus ride from my base town to the nearest city or train station. I don't think anyone has mentioned that Cortona is a hill town, so its train station is accessible only by bus or taxi. That's not a situation I'd be happy with for 9 nights. With a rental car, it might be just fine.

We have been everywhere on your list except Chioggia.

I would go mad in many of these destinations for as long as you (or Chat) have planned without a car, especially in possibly rainy/dreary weather with off-season/limited hours for sites and public transportation.

In Puglia, there's enough to do in Lecce and good/decent transportation options. Not sure how Ostuni would feel. Monopoli would be okay.

Nine nights in Cortona? Six nights in Gubbio? Seven in Urbino? In early spring without wheels? Hmm.

But of course it depends on what you like to see and do. In any case, I would look very carefully at local bus and train schedules.