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Day Trips in Tuscany from Florence: should we do a wineery tour? What else?

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At the end of June/early July, my two friends and I will be staying in Florence for 5.5 days. We have decided that we would like to spend a couple of those days on day trips in the Tuscan country side.

Last time I was there I took a wine tour that included two wineries and a grappa distillery. It was organized by the hostel I was staying at, and was fairly inexpensive (that's what I remember thinking, but I can't remember how much it was anymore) for everything: wine and grappa tastings, snacks at one winery and lunch at another, as well as transportation and a knowledgeable and very chipper tour guide. I really enjoyed it and this is one of those times where I WISH I had bothered to keep a journal or travel log or something, so I could book with that company again. It was really nice!

Anyway, on to my questions:

I'd like to do something similar for one of our day trips this time, and I'm wondering, first of all, if it would be more economical to book a wine tour of some kind or to rent a car for a day and try and figure things out for ourselves. I know next to nothing about doing either so any advice is welcome.

If you think we should just rent a car and visit a winery or two on our own, can you recommend a winery or two for us to visit?

If you think we'll get more bang for our buck with a tour, Can your recommend one? Hopefully with lunch and/or dinner included? I'm hoping for something that isn't super expensive but I'm not entirely sure what is reasonable to pay for a wine around 100 euros completely unrealistic? Don't laugh at me if it is, I really don't know!

Questions part 2:
I'm also wondering if anyone can suggest something for us to do on our second day trip. We've considered Sienna, but really we want to see as much of the countryside as possible, maybe with a small village or two mixed in. Sienna sounds lovely and we aren't necessarily dismissing it, but our trip is a bit city-heavy (Paris, Nice, Florence and Venice) and so we want to include lots of nature for our day trips. But please feel free to recommend Sienna if you feel it's a must-see!

tl:dr version: Should we rent a car for two days and drive around to see small towns and wineries? Can you suggest some wineries? Should we rent a car for one day and take a tour on the other? Can you suggest a tour? should we just stay in Florence after all? If you've got an opinion, I want to hear about it :)