After arranging this trip in 2020 well, we know how that turned out, we ended up going in Sept of 2023 and what a trip it was!
We flew into Milan and stayed 2 nights - did a walking tour
Venice 3 nights - did a evening doge’s palace/basilica tour and a food tour
Cinque Terra 2 nights - did our own thing
Florence 3 nights - Tuscany wine tour and Academia museum/david tour
Sorrento 6 nights - day trips Amalfi and Capri
Flew out of Rome 4 nights - golf cart night food tour
Most of the hotels were amazing and I booked tours at each location. We took the train everywhere and we felt like we were on the amazing race trying to find the correct train but it all worked out. We dodged a train strike that was looming on the last leg.
What an amazing place on earth.