This trip was seventeen days, and we did 2 nights Milan, 2 nights Varenna, 3 nights Monterosso, 4 nights Florence, 4 nights Sorrento and 2 final nights in Rome. It seemed to be the perfect amount of time to spend in each place (as I've already been to Florence twice and Rome three times). We never felt rushed. Hotels in all cities were wonderful, but I'd like to give special notice to Villa Steno in Monterosso and La Favorita in Sorrento. Those two were truly outstanding and I would go back in a heartbeat!
Places that were new to me on this visit were Milan (loved the big-city vibe and the Duomo area), Lake Como (can really recommend Villa Balbianello; just a beautiful spot), and the Cinque Terre. We are not big hikers, but really enjoyed the walking tours of each village provided in the Rick Steves guides.
In Florence we took a wine tasting tour of Montepulciano, Montalcino and Pienza, which (although it ended up being a big bus tour) we really enjoyed. We also took a trip to Assisi which was wonderful -- would like to spend more time there. In Florence itself, the Duomo Museum is not to be missed!!!
In Sorrento, we managed to get to Capri in spite of threatening weather, and also took the Circumvesuviana train to Pompeii. We also took the shared Rick Steves/Mondoguide tour of the Amalfi coast, which was great but we didn't really get to see a lot of Positano as the driver parked at the bottom of the town and the pathway up is super-steep! Loved Amalfi and Ravello, though.
In Rome, the one new (to me) site we visited was the Capitoline Museum, which was fabulous...don't know how I'd missed it before. Going to Mass at St. Peter's was also a highlight, especially for my very Catholic sister.
I managed to misplace my 2017 Rick Steves Italy book (probably during our last taxi ride in Rome), but I have replaced it and am busy highlighting all the things we saw...makes a great souvenir! I welcome any questions.