I gleaned a lot of good advice from reading the posts on this site, so I'd like to give back a little. Late September, we went to Lake Como (stayed in Bellano), Monterosso al Mare (Cinque Terre), and finally Florence.
We stayed at a nice little Air BNB flat in Bellano, called Missultin. Bellano was actually a nice place to base. We took ferries all over, even during torrential rain storms. Bellano was a little oasis of peace after all the crowds, and the restaurants were really good. It was nice to walk around in the evening peace. I preferred Vernazza to Bellagio. Bellagio was incredibly crowded and very expensive. Vernazza is a bit more charming, although crowded as well.
In Monterosso, we stayed at an RS recommendation: Hotel Marina. Def recommend it. A short walk from the train station in the old town, a lovely little place. The room was spacious and clean. The breakfast was good. We also had dinner at Ristorante Belvedere, another RS recommendation. Thank goodness we reserved in advance as the place was overflowing by the time we left. We had a nice table overlooking the beach. The mixed seafood for 2 was delicious.
Hiking the Cinque Terre was not what I expected. Our plan was to do the walk from Monterosso to Vernazza, have lunch, then hike from Vernazza to Corniglia. We left at 8:30 am on a nice day for the first walk. It was much more difficult than I expected. There are a lot of steps and most of them are very steep, esp. for my short legs. It ended up taking us almost 2.5 hours. Although we are used to hiking, we are not used to the very uneven terrain and it was necessary for us to stop and take breaks often. Most people did the same. Obviously seasoned hikers had difficulty. We didn't make the second hike that we had planned on. In hindsight, I wish we would have taken the train to Vernazza, hiked a little ways towards Monterosso (10 min.), taken the gorgeous scenery pictures at that time, gone back to Vernazza, and then tried the hike to Corniglia.
In Florence we stayed at Hotel Garibaldi Blu. A short walk from the train to Piazza Santa Maria Novella, and easy walks to all the sights. It's a nice, small hotel. A bit expensive but we wanted a bit of a splurge for the end. 2 restaurants to recommend: Trattoria dall'Oste (a fabulous bistecca, great service) and Degusteria Italiana (we had lunch from the tastings menu and it was perfect).
We had thought we would take a look around the shops for leather coats and we looked at ones that various sites and people had recommended. We found some nice ones, but they were far too expensive. Finally, we went to La Pelle (near Ponte Vecchio, RS and friend recommendations) and were very pleasantly surprised. My husband and I both found leather coats that we really loved and for a very good price. We needed the sleeves altered but they told us that was no problem, especially as we were leaving in 2 days. Four hours later we found out that our flight to leave was canceled and we had to rebook on one leaving the next morning! La Pelle then showed us what great customer service they have and arranged to have the alterations done immediately. We ran back to the store and were able to pick up 2 coats that fit perfectly and that we will be proud to wear.
We haven't been to Italy in about 20 years. While I was prepared for it to be crowded, I was surprised at the literal hordes of people, especially in Bellagio and the Cinque Terre. When Rick Steves says "hordes", he means HORDES. MANY tourist groups of 20-30 people. Regional trains literally packed wall to wall. I definitely would not go at the height of tourist season if I could avoid it. Definitely make restaurant reservations if there is somewhere you particularly want to go. We made a few reservations for 6:30 dinner. The restaurants were packed directly after that.