You're gonna have a great time!! We were there last year. I brought my own cigars but saw a couple shops along the way but nothing that stood out. And, as mentioned above what I saw was expensive. Regarding dining, I was stressed out before the trip as to the right places to eat..... no need to stress! There are sidewalk cafes everywhere and never had a bad meal. One that sticks out was Cafe Concerto Paszkawski on the square across the the Duomo in Florence. There was a lady opera singer with a beautiful voice on the square while we were enjoying some wine a nice meal and a cigar. Almost surreal.
We did pay for day passes on the "Hop On - Hop Off" buses in most of the cities we visited. Pretty handy. The The Sistene Chapel and the Vatican tour is all you expect and more. Can be crowded but worth the hassle. Have a great time and travel safe!!