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Pienza or Montepulciano? And advice on airport logistics (departure)

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Hello All,

I have a multi part question here:

Part 1) I’m wondering if anyone can draw some contrast between Pienza and Montepulciano. I understand that Pienza is flatter and that can make negotiating a car in and out easier, and that it is a bit more centrally located. Here are some specific ways I’d like to know how they stack up but I welcome other insights as well.

The views – does one offer superior outward views of the valley/countryside?

Liveliness/activity in town – does one town shut down earlier than the other? Does either one have more folks still out strolling and hanging out in cafes later into the evening than the other?

Flowers/beauty – this might be silly but when I Google image Pienza I see more flowers & plants on sills, planter boxes and more climbing plants along walls & buildings, etc. than when I Google image Montepulciano. Is this accurate? Is Pienza more flowery?

I am struggling between these two, and I don’t think I can go wrong with either one but I do need something to inspire a final choice.

Part 2) I have gotten the impression that Siena is best at night, both because day trippers have gone and because it lights up nicely at night. I don’t know if I should make Siena a day trip from Montepulciano/Pienza or stay 1-2 nights in Siena. This is still tentative, but I’m looking at between 6-8 nights total in this part of Tuscany. Do I stay 2 of those nights in Siena? This also hinges on getting to the airport in either Pisa or Florence. Pisa is preferred for flight schedule. Is it possible to leave our hotel in Siena bound for either of those airports for a same day AM flight whether by train/bus or by private driver? Or must we stay in our departure city the night before? If we must stay the night in the departure city then that probably dictates keeping Siena a day trip as I do not want 3 different overnight stays inside of 7 days.

Part 3) Does anyone have any experience with airbnb? I have not used them before and I don’t know anything about their reputation. I browsed some good looking and well priced properties on their site though. And how crucial is air conditioning in Pienza/Montepulcino during the tail end of September? Would choosing accommodations without AC be a big mistake?

Thanks a bunch!

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