In Emilia-Romagna, I’ve stayed in Parma and Bologna, and taken food tours from each (Parmigiano Reggiano cheese, Parma Ham/Prosciutto, Balsamic Vinegar), but Bologna’s my favorite. For a city with an historic core, it’s very walkable, and without as many blockbuster sights as, say, Rome or Florence, it doesn’t have the same touristy feel. The tourism office downtown does walking tours, and the Two Towers, a number of churches, and a handful of interesting museums provide some decent sights. The food, though, is perhaps the biggest attraction. Take train to and from Bologna, and be on-foot in town.
Tuscany has phenomenal places - Florence and Siena are Renaissance All-stars, with understandable tourism. A much less touristy part is the Etruscan Coast, in southwestern Tuscany. We’ve gone the past 2 years, in late September. Home base is Castagneto Carducci, a hilltown with lodging in or around the area. A rental car is pretty much needed, and by far the best outfit is Lu.Ma.Tos . Here’s their Website, in Italian only https://www.lumatos.it/noleggio-pulmini/ , but e-mail them and Thomas or another person will respond in English. We arrived by train in nearby Donoratico, and they met us at the tiny train station with our Renault. Dropped the car off to them at the station when we were ready to take the train out. It’s a wine region (Bolgheri is 5 miles away), plus access to the seaside, and Etruscan tombs along the coast to the south. There are also ancient small towns down twisty mountain roads (like Sassetta and Massa Marittima), and you could even catch a ferry out to Elba, if Napoleon’s exile island is of interest.