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Tuscany: Which town(s) to stay in if main priorities are wine & food?

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I've already posted a similar question but I am still not clear so hoping more people will answer this topic :)

My husband and I will be visiting Tuscany, Piedmont, Umbria and Bologna from Sept 22- Oct 10th to celebrate our first wedding anniversary. Our main priority is food, wine and views. We are planning on staying 5 or 6 nights in Tuscany and I am certain I want to stay in either Montalcino or Montepulciano. Where I am confused is trying to decide on just staying in either of those towns OR staying 3 nights and then changing to the Chianti area for for 3 nights as well. We will do a day trip from Florence from Bologna and won't be visiting Siena. Is there a big difference in the regions where you feel we should really see both? So confused, please help!

Also, if anyone has a cooking class they would recommend that would be helpful too!

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