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Umbria Tuscany and possibly Amalfi coast - help!

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I need some advice! My girlfriends and I are traveling to Italy for a little over a week. We are thinking of flying into Pisa and maybe staying in Tuscany overnight to go to a winery that day or the next day. We'd like to rent a car from the airport. How easy is that?
My girlfriend wants to go to the winery that started the super Tuscan (sounds good to me). Suggestions on a nice place to stay?.
Then-we thought we would travel on to Umbria. We would love a place that's not in a city, but more in the countryside. Worried that it will be too much like a b&b though. We all like the feeling of anonymity (somewhat) that a hotel affords one. However the country is very attractive. Suggestions on where to stay?
Two more things- we want a cooking class that is one or two days or two separate days. Suggestions?
Lastly, how crazy will it be to go to the Amalfi coast in August ???
Any advice is greatly appreciated!! Also -its my 50th birthday so I don't mind spending a bit more and we're all very active!
Thanks a bunch!!
Leaving and flying back to USA out of Rome

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