My wife and I will be spending some time in Florence and will be doing 2 day trips. The first one is going to be a trip to Pisa and Lucca. We're undecided on the second. We would like to see maybe a couple towns and also visit some vineyards and do some wine tasting. I definitely want to see Sienna and also go to Greve, but I wasn't sure if there was a tour that encompassed another town or two or if it would be worth squeezing that much into one day.
'Walks of Italy' is a very highly regarded tour company; this tour https://www.walksofitaly.com/florence-tours/tuscany-day-trips-from-florence might fill your needs.
I would second Walks of Italy.
Take a look at tuscantrails.com, tuscan-wine-tour.com, and tuscanyuntouchedtours.com also. And look at I Just Drive.
We have not done this Walks of Italy tour, but have loved the others that we did.
Another option is tours by Roberto Bechi, a guide Rick Steves uses a lot in the area. www.toursbyroberto.com will give you lots of information. If you click on "Joinable Tours" and "Calendar" you can get an idea of the many options he offers.
His tours are in an 8 person van, and he will pick you up at your hotel. He like to go to off-the beaten-track places and share parts of Tuscany not necessarily covered by others. He gets great reviews here and on Trip Advisor.
I really like a whole day in Siena, every time we stay in Florence. I took a day tour the first time I visited but now we just catch the sita bus (next to the train station) and stroll around because Siena itself is amazing! As for Wine tours, if you would like one that doesn't extend too far into your evening, Tuscan trails will do one every day but Sunday (small group of 8 or less) to Chianti and visits 2 estates, with a very full lunch included. Plus, Todd is great and so personable. Italy & Wine goes to montepulciano and montalcino once or twice a week but the tours extend past 6pm, as they are further.