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Southern Tuscany itinerary help for early June!

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My husband and I will be heading to Tuscany from Florence for 5 nights in June (we have 5 full days). Our current plan is to stay in Sinalunga at Locanda Dell Amorosa and do day trips from there. I am also debating whether or not to stay in Siena for 2 nights and Sinalunga for the remaining 3 since there seems to be much to see and do in Siena. I am struggling with the itinerary logistics and which cities to group together. We would like to see Siena, Montepulciano, Pienza, Montalcino, Chianti, San Gimignano, Volterra and Cortona. We plan to hire a driver to take us around. Does anyone have suggestions on 1) whether to spend 2 nights in Siena or all 5 in Sinalunga 2) how best to see the cities over 5 days? Thank you!

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