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Chianti wine/food tour help

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In August/September I will be traveling to Italy for the first time by myself. I have booked the first 5 nights to stay in Florence, then I am hoping to divide the remainder of my time between Siena, the Chianti region and Cinque Terre. I am looking for recommendations regarding my time in Siena/Chianti; I either would love to find a 3-4 day group trip that would combine wine tasting, culinary exploration, all transportation and lodging or it looks like I will be renting a car and be making my way through the Chianti region. I know there are some very expensive tours I could have put together for me but I think it would be fun (and cheaper) to join a group for a couple of days with a pre-determined itinerary.
This is my first big trip Ive planned for myself and Im feeling overwhelmed by the possibilities and I would really appreciate any advice people may have...
Any ideas?

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  1. Sounds like a great trip!
    I can recommend Judy Witts, 100%, who runs great wine and cooking tours in Chianti. Here is her web site:

    She is the perfect person to help you. She's about to come out with an app too, but don't know if that is out yet.