Been there - Looking for suggestions for new ideas

Time of year? Car or train?
How about Sicily?

Bologna is a great place to visit - I’ve been three times. It’s the “food capital” of a food-focused country! Lots to see and do in town, too.

Also, we just visited Puglia (the heel of “the boot” of Italy) a month and a half ago, and are already considering going back to see more. There’s unique food. It’s a huge wine and olive oil producing region. Castles, forts, stunning hill towns with unique architecture. We’ve been to places you’ve mentioned, but this trip was different, and also included starting in Naples. Naples had plenty of people, but the towns in Puglia were pleasantly uncrowded. We didn’t go to any beaches in November/December, but there are beaches. There are also national parks, including Italy’s biggest, but we didn’t visit them this tone, either. Although we took trains to go from Bari to Naples at the end, we had a rental car to get from Naples to Altamura to start off, and stayed in Altamura, Lecce, Martina Franca, and Bari, driving to many other towns during our stay. If I had to pick one place to stay, it would be Lecce if I wanted a smaller city, or Martina France for a quaint Old Town. Bari is really big. You’d need to study train/bus options if you weren’t driving.

Towns in Puglia were getting fabulously decorated with Christmas approaching, but it rained quite a bit during our stay. Weather could be nicer other times of year, but more tourists might be there, too.

You could spend a lovely week in Trani, in northern Puglia. It’s a pretty little town with a busy harbor, several historic churches and some great restaurants. Some interesting day trips nearby — Castel Del Monte and the salt plains at Margherita di Savoia. It was one of our favorite stops in Puglia.

The lakes are just like the lakes in Wisconsin? Well, they’re filled with water, they do have that in common. But otherwise, I think your friends may have had a few too many Wisconsin old fashioneds to say that. But more seriously, you’ve seen a lot of the top half of Italy, try the bottom half, whether Naples, Pompeii, Amalfi Coast, Sicily, etc.

I stayed in Bologna for a week with several day trips within Emilia-Romagna. If you plan to rely on trains, Bologna is a good choice with easy access to Ravenna, Parma, Modena, Ferrara, Faenza and other places. In addition to all the good food, there is also quite a bit to do and see in Bologna (uncrowded museums and churches you can walk to) but, at least in my experience, nowhere that needed advanced tickets which was nice. Many of the mosaic sites in Ravenna do often need advanced tickets.

Bologna is fantastic! There are a lot of good day trips from there, although I’d do (and have done) Ravenna as two-three days on its own. Further off the American tourist circuit, have you considered Aosta Valley? I spend a lot of time in Wisconsin and can’t imagine comparing the lakes there to the Italian lakes. Completely different.

Will you rent a car?

I loved Bologna so much that this year I'm going back for a 6-night stay, mostly for day trips this time. There's an interesting Jewish quarter worth exploring, tour the medieval university rooms. More day trips than have already been named - Bologna is a rail hub, so it's easy. I'd try to find a place about half-way between the train station and the main piazza so you are walking distance to everything.

"but my friends say it's just like the lakes in Wisconsin"

We in the upper midwest can be a little parochial, but your friends' comments might be the an all-timer. It's like comparing Sturgeon Bay with Venice because they're both on the water. It's like saying TJ Rubley is pretty much the same as Tom Brady because they both played QB.

The lakes are beautiful. Full stop.

But as someone above pointed out, you've see a lot of the north. Have you thought about Sicily (Palermo?) or the south? What about Dubrovnik and the Dalmatian Coast islands (very Italian-esque and easy for travel)?

It's awesome you guys are traveling at 77. You are an inspiration to me.