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Visit Chianti and Siena in 1 day-Realistic?

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HI,
I am visiting Florence for 5 days in early August and would like to make 1 or more day trips to the countryside. Is it possible to visit Chianti (wine tasting) and Siena in the same day? Or should I do a day for each? I like a relaxed pace (wine tasting, picnic, exploring, etc) versus a fast pace. I won't have a car so am considering taking the bus. Can you wine taste without a tour? I really enjoy visiting the wineries and enjoying the countryside vs. wine tasting in an enoteca. Do tour prices include the wine tasting? Can you wine taste in Chianti without a car? Are there certain days to avoid, for instance are most things open in Siena/Chianti on Sundays/Mondays?

Thank you for your help!

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