7 days and a wake up

A rich and full itinerary! Fai buon viaggio!

I like your itinerary.

I hesitate to recommend restaurants, because everyone's taste is different, and even a good place can have an off night,mor a surly server. But I will mention a few places we really liked and found reliable.

In Verona, Osteria Il,Bertoldo (once you find it) offers lovely ambiance and a warm welcome, with an interesting menu and good prices. They had recently opened when we were there in 2010 and I see they still get excellent reviews. The owner's response to the one negative review on Tripadvisor is amusing---it seems they do not even offer the dish the person complained of so bitterly.

In Florence, we really enjoyed Del Fagioli, a humble trattoria with no English menu and shared tables, most with families. We were the only non-Italians that night but were made to feel very welcome. The food was delicious ( assuming you like meat dishes).

In Venice, where we spent a month, we mostly cooked in our apartment with the fresh fish and veggies from Rialto market. But we found a couple of places we returned to several times, because the food was good, the ambiance pleasant, the waitstaff friendly, and the prices moderate. Neither is particularly frequented by Venetians, who are vastly outnumbered by tourists in most restaurants.

Taverna San Trovaso ( not to be confused with the Ristorante by the same name) is right on a canal in Dorsoduro near the gondola workshop. They have a nice grilled seafood platter to be shared by two. Make a reservation so you can sit in the nicer back room. I believe this one is a Rick's rec but don't let that discourage you.

Rosa Rossa is a restaurant serving pizza and typical Venetian menu on Calle Mandola, near La Fenice. It is famous as Johnny Depp's favorite place but we loved the atmosphere, the friendly waiters, and the food (I confess I love the Italian way with fried shrimp and/or calamari and they do it right---very light and crispy.

Bravo! Nice plan!

As to restaurant inspiration:

For Venezia, we are working our way through this list. Ai Artisti is the favorite so far. Do reserve. We also like to have a pizza at NoNo Risorto (Rick Steves' pick) every trip and are very fond of Da Remigio where we found not one tourist besides ourselves. Absolutely reserve as they get busy!

In Bologna, Drogheria della Rosa is delightful and an adventure. They pretty mich tell you what you are going to eat and it is all fabulous!

In Roma my list is large. I will send you a PM.

I like it, good itinerary.

Venice, I would suggest you buy mutli-day vaporetto tickets to save money. You can just jump on and jump any boat anytime. Very convenient. I don't know if your Venice card covers that, but I doubt it. Also, De Mamo for a nice, casual dinner. Taverna San Trovoso isn't bad either.
Bologna, you have an opportunity to go to San Marino from here. It isn't a train trip though I don't think. But, how many times will you get to see one of the smallest countries in the world.
Lucca, be sure and walk the wall. Also, a day trip to Pisa might be n order, it isn't that far. You might try Monetecatini on the day trip, it is a train stop on the way to Florence from Lucca
Florence, see Piazzale Michelangelo
Orvietto, you will be walking some hills. If daring go to the bottom of the well, if not, stay on the top and look down!
Rome, try to see the Borghese Gallery, great sculptures.
Great trip, enjoy.

As a fellow traveller, also over 60, who just returned from a two-week solo trip to Italy, your phrase "some leg issues" felt familiar. Be aware that at some of your towns, when you arrive at the train station, you will need to walk DOWN a long flight of steps to a passageway that goes under the train tracks, then UP a significant flight of stairs to the train platform. You will repeat the process when you arrive at your destination. This will be true in at least in Lucca, Ravenna, Orvieto (I believe), and maybe Bologna (and maybe Verona; it's been awhile since I've been overnight there). When packing, consider that someone will need to heft each suitcase up and down the stairs, so smaller (with wheels, for many of us!) is almost always better! Once you are on the train, there will be places to put your bags, either above your seat (my rollaboard usually went there), or sometimes behind the seat. There are also sometimes luggage racks near the doorways.

A Rick Steves Italy book will have restaurants for every town. I wouldn't go without it, personally.

A tip for Siena -- Climbing the Torre Mangia is fabulous (https://janettravels.wordpress.com/category/siena/) but if you are not up to narrow winding steps in old towers, you can access a wonderful perch with a birds eye view of Siena from the Art Museum. You can enter a passage to the top of the uncompleted Cathedral wall from one of the floors of the art museum (they stopped during the black death due to the epidemic and due to incompetent architects). There are a few, but not many steps and you have a great view from the top of the wall out over the city.

The Cathedral is something else -- be sure you save a couple of hours for enjoying its magnificent interior.

I think Orvieto train station has an elevator now. Many cities are installing elevators, but there are still many with the sottopassaggio (stairs).