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Best stop between Florence and Cortona and favorites near Montepulciano?

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We are heading to Cortona in May for a week in a villa with friends. We will be driving from Florence to Cortona and we're interested in peoples thoughts on the "best" one stop between the two towns? We've done Chianti before on trips but just curious on a can't miss stop. The two that caught my eye were Castello di Brolio (but it sounds a little touristy and I saw the word tour bus in several reviews) and Castellina in Chianti.

We are also going to do a day trip from Cortona to the Montepulciano area and curious on any can't miss stops or wineries around there? We tend to like great wine but prefer smaller mom and pop producers. We live in Napa Valley and have always found the small family owned producers tend to be much more fun (and better wine) than the large glitzy spots.

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