re: Italy Vacation November 2017 - May 2018 Timeframe

Venice is incredible to experience the city but not as 'Italy'. It's probably twice the price as anywhere else, there are some grocery stores I'd eat mostly there and maybe pizza for dinner. Then save your money to eat out in other cities. I spent 5 nights there and we really enjoyed it, but I'm not sure if recommend that. I've been to the beach there, all the islands, etc. I'd do the main city one day and then the islands the 2nd day. The boat transportation is like $25/ day or something if I remember right. If you are planning way out id highly recommend getting an apt with a balcony, and I'd get pizza for dinner and a bottle of wine and eat dinner there every evening.

Italy is the one country where you can close your eyes and open them, and it's hard to believe how incredibly 'italian' everything looks. I've been all over Europe and it always sticks out as being so cultural.

As said, pack as little as possible. You want to be able to walk a couple of blocks and get on and off trains easily.

If you plan far enough out to find decently priced hotel rooms it's really rather affordable.

Drink the house wine carafes. Don't order bottles at dinner, a carafe is like 3-5 euros and most locals drink it.