Ciao Ping Guy,
I saw you posted your questions in two separate posts so I'll answer all your questions in just one spot.
I believe your itinerary for your first day from Florence to Siena is good, breaking it up works well, especially since you do want to stop and do wine tastings/winery visits along the way.
The second part, from Siena to Montalcino to Montepulciano to La Foce, hot springs and on to Rome, seems to be too much for a day, so we're you planning on stopping for the night somewhere before Rome? Then continuing on the next day? By when do you need to be in Rome on the 16th? You also do want to spend some time in Siena the evening and morning before heading off...
If possible, I'd suggest an overnight in the Val d'Orcia area... where depends maybe on when you need to be in Rome the following day.
All the stops are very good places to go through, the hard part will be not stopping too many times along the way to enjoy the views and take photos. The one place you skip altogether which merits a visit is San Gimignano but maybe you've seen it before or maybe get a chance to see it while you're in Florence visiting your daughter? If you can, do so, you won't be disappointed.
In Siena, I highly recommend
Hotel Athena (it has parking but right on the walls so you don't have to walk to see the sights). Not too far from the hotel is the trattoria
Da Nonna Gina, I recommend that for dinner the day you get to Siena. It is a small family run place making local favorites like pici, we always go there when in Siena.
As far as the weather, it generally is still good - mid November I'd suggest just dressing in layers since you can have cool mornings and evenings but have warm sun in the middle part of the day. Wineries are open but I'd still contact them ahead of time and ask about hours, you definitely want to make sure they are open on the specific days you're planning. Yo shouldn't have a problem but if their hours are different, they might anyways open for you considering you are a small group and not just a couple. Did you have specific wineries in mind yet for Greve and Montalcino, aside from the one you mentioned (Le Ripe)? I assume at Badia di Passignano you're talking of the Antinori estate, they do have their winery nearby in Bargino and cellars at the Badia but you might need to book ahead to see those. They also have the restaurant next to the Badia, we're you thinking of lunch there? You definitely have to book that one!
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