Tuscan Honeymoon

I'm going to Tuscany for my honeymoon for two weeks in late May/early June. I'll be on the Ligurian coast to start, but then will be near Maremma (and Ornellaia/Sassicaia/Antinori) for a couple of days, and then in Florence for the second week. All I've read has gotten me very excited. I'd like to buy some good Tuscan wines to enjoy back here in Virginia. I was hoping the forum readers might have some gems of wisdom for me regarding my questions below:

1) Will I find the best $$$ deals at the wineries, or are the wine shops in the towns going to have pretty good prices?
2) What is the best way to find interesting wineries that are visitor-friendly? Should I make appointments, and if so, how far in advance? (I don't speak Italian, btw)
3) Due to budget restrictions, I'd like to buy several bottles in the $30-60 range, and take a few precious bottles in the $60-100 range home as well, maybe a case in total. Any thoughts on a good buying strategy?
4) What vintages should I expect will be available to taste and purchase?
5) If I end up with a case of wine (or two), should I ship it back, or try to carry it back (and presumably pay some import tariff)?
6) Anything wine or winery related that I should just not miss?

I've looked at some websites with related info, but I'm hoping some of you have some good ideas for me. Thanks a lot!
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