Traveling in Tuscany

Check Montalcino and Montepulciano area wineries. Those are the best. Friends of mine traveled there a few years ago, enjoyed it a lot. Can't remember the names of the wineries, but I guess any of those are of great quality, serving local cheese, bread and other delicacies paired with the perfect wine. I'm pretty sure other's will advise a lot better

For festivals, you can find lots of info here:
https://www.discovertuscany.com/tuscany-events/september-in-tuscany.html