Our one trip was Bike across Italy with Ciclismo Classico. It was very expensive, and worth it. You will want to do some training, there are a couple long days. Outside Rome, I had people go out of their way to be nice, even be encouraging. One particularly nice dinner we had, we walked out in the morning, and I noticed an ad, the dinner would have been over $100 without the wine.
https://ciclismoclassico.com/tours/bike-across-italy/