Having been there, I would say expect a nightlife should be on the list, there is literally nothing to do at night. Don't book Venice for several days, see some glass blowing, get lost in the narrow alley ways, and book it to Tuscany for wine and food as soon as you make your way around the city.
I love the "don't wear shorts, people will make fun of you"...I wish they would make that rule for shorts and fannie packs in Vegas, but then how would we be able to tell the Mid-Westerners from everyone else.