Choices to make...suggestions?

6 nights = 5 full days (plus maybe some hours on the day of arrival and the day of departure, which I don't like to even take into account)

2 full days will go for Florence alone.
1 full day Pisa/Lucca (by train)
1 full day Siena (Bus/train or automobile)
1 full day is available for an afternoon relaxing drinking in the Chianti (by rental car or hired car with driver)

You can attach San Gimignano on the way back from Siena.
You can also attach San Gimignano together with the Chianti, if you have a car.

Putting Siena+San Gimignano+Chianti tasting all in one trip is doable but kind of rushed, IMO.

Pisa is very easy to do on your own. But if you are going to Pisa JUST to look at the leaning tower for 5 minutes, I wouldn't bother. I spent a half a day there and saw the museum, the baptistry (which is amazing BTW), the graveyard where I found the burial sight of Fibonacci (a famous mathematician if you didnt know), climbed the leaning tower (get tickets well in advance if you desire to do this) and enjoyed the duomo.

Siena is certainly worth a day trip, or even a couple days. I did an overnight stay there and wished I had stayed longer. I have not seen any of the other places on your list so I can give no opinion. It would be an easy thing to do to join a group on a day tour to see multiple towns or to visit wineries without the hassle of renting a car and trying to do it yourself.

Thank you both for your thoughts. I think Pisa and Lucca may be the short straws on this trip. I feel more strongly about Siena and San G, and wineries and olive oil! I prefer to be more spontaneous but my husband likes to have things set.

Any great restaurant recommendations from your travels? Not tourist places, but more off the beaten path types? Thanks?

We just got back from Florence and wonder if the tour you referenced is the "Best of Tuscany Tour" with Walkabout Florence?
We ( Grandpa , me and 17 yr old son) took that tour-which went to Sienna, lunch at a winery, San G and then Pisa and enjoyed it very much. (I also usually don't like big bus tours). The guides (both the one on the bus and the one for Sienna were very knowledgeable and entertaining, the lunch and winery tour was excellent. We enjoyed Pisa much more than we thought we would as the guide gave us so much more of it's history than just the Leaning Tower- which was amazing. We saw a lot and got to do a lot with minimal effort on our part - which I have to say was kinda refreshing and relaxing! My 17 yr old and I splurged for the add-on option of the ticket to climb the Tower and it was worth it.
We did not feel rushed at all - had adequate time at the Cathedral in Sienna and in the Campo as well as in the other places.

we did academia museum in Florence in the am (had reserved tickets) and then took train out to Pisa for 3pm tower climb (had reserved tickets) all doable in one day, however, the mistake we made was getting off at the town center train station instead of the one closer to the tower......and surprisingly, there were very few (ok NONE) signs to the tower in the first mile we hiked,,,,,, and once on tower grounds, our group of four got separated (I was still holding the tower voucher for the whole group)..........ok, so I'm talking more about my own trauma than the tower. just saying, its doable in one day, especially if you are more organized than we were. in Florence, I recommend the White Boar for a hearty dinner.....cute wine jugs. ((part of what added to the anxiety was.....the academia voucher had to be presented to a ticket office about one block away and exchanged for tickets before we lined up. after getting separated on the way to the ticket office at Pisa and wasting about 30 frantic minutes trying to find our colleagues(afraid we would miss our timed tower climb).......were told we did NOT have to exchange that voucher......just take the paper I printed off in the states directly to the tower line. sigh )) PPS.....I don't do heights at all, so I toured the baptistery instead and then sat in the lobby at the aforementioned ticket office waiting for them.....there is a very cool film of attempts thru the centuries to straighten the tower......its free and you get to sit in the air-conditioning......

If you were more pressed for time, you certainly could reserve the Uffizzi Gallery for your arrival afternoon (or don't reserve if you're buying a Firenze Card); enter by 16:00 to have two hours inside. My first side-trip priority, both for proximity and sightseeing, would be to take the [bus to Siena](www.sienamobilita.it) and spend a full day there at your own pace.