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After Heart of Italy Tour

After the completion of the Heart of Italy Tour in Florence, we, along with another couple, want to visit Siena and Montepulciano and then return to Florence to fly back to the US. Should we travel to Siena first and then Montepulciano or Montepulciano first and then Siena?

What is the best way to get to these two destinations from Florence and back? We plan to stay at least 2 nights at each location. Is this agenda possible logistically? Also, any recommendations for accommodations would be appreciated.

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Are you driving? Or using other transport? You can get a bus to Siena from Florence. I don't know about the transport options to Montepulciano but maybe others will chime in.

If driving, I personally would pick Montepulciano first since its a little further, making your trip back to Florence for your flight slightly shorter from Siena. If you do have a car, you'll want to make sure you have a plan for parking, especially if staying in the center of either one.