Oh, don't worry Thorn, I will be shopping in grocery stores. Food is one of my main hobbies

What did you mean about putting your helmet on the outside of your bag? I was planning on putting mine in my checked luggage.

I always take the approach that if I don't bring the clothing item with me, I will not have it. I'm a size 2x/18, and I can't imagine the clothes shopping options will be great for me in Italy. Also, that means my clothes are bigger, so I get to take bigger luggage (that's one of my favorite rationalizations).

I will try to really limit what I bring, but I plan on tipping the guides well for lugging it around for me.