Spiff,
sorry if this is long. I just have so many good memories from my trip to Italy.
Great suggestions from OSB re Tuscany. Frommer's Guide is great, as is their Italy for $70 a day - it includes guides for the Uffizi Gallery and Accedamia in the book, so you don't have to buy them at the museums. I agree on the food - tuscan food is so much more varied and different than what you see at your typical Italian place in the U.S. Wild Boar, suckling pig, rabbit - all worth trying (although I did feel a little guilty about the suckling pig.)
My advice is do not try to do too much. My wife and I spent two weeks of our honeymoon in Italy. Three days in Venice, 8 in Tuscany, and 3 in Rome. I am a history buff and felt obligated to visit every museum, statue, fountain, hill town, castello. After 1 marathon day of visiting Montalcino, Montepulciano and Siena, my wife told me that we would not leave the villa the next day. We hunkered down with a few bottles of wine, read books, walked around the farm, enjoyed the fresh air, etc. I was surprised that I did need a breather. the trip was much more relaxing after that when we were more selective of what to see (hopefully we'll go back again and again!)
Towns - OSB is on the money. However, I would sub in Montalcino instead of Montepulciano, especially if you are making this a wine trip. The enoteca at the castle in Montalcino has tons of Brunellos available by the glass as well as great local cheeses and sausages. The castle is also impressive on it's own with these massive stone walls which you can see for miles as you drive towards it.
Also drive up and down the 222 through Chianti - it's similar to Rt. 29 in Napa with wineries off to either side, although definitley not as commercialized as Napa.
FYI - the main museum in Florence is the Uffizi Gallery - Well worth it for the Renaissance paintings, Birth of Venus etc.
Also - Climb to the top of the Duomo in Florence if you have the time, it is well worth the effort and the view from the top is breath taking (literally and figuratively after climbing 700 plus steps).
cheers!
DL
