2 nights in Montepulciano + 1 night in Pitigliano

I won't be the only one to ask, so let's get this out of the way--what kind of scooter are you talking about? Nearly three hours on a scooter sounds like hell to me.
I have not been to Montepulciano, but I know you could fill a weekend there. Since you will be living in Florence (lucky you), I'd visit both towns on separate weekends. I have visited Pitigliano, and in addition to the gorgeous town itself, there is so much to do in the area, I don't think you would have any regret whatsoever about giving it a full weekend. Nearby, you have the springs at Saturnia, the Etruscan sites at Sorano/Sovana, and many examples the evocative trails known as Via Cave. Plus there are lots of pretty hills towns, and once the weather warms, some of the finest beaches in Italy.

Hi Vala! Fair enough about the scooter. Tbh we're not particularly worried about that. We traveled for two months across 4 Indonesian islands right before the pandemic hit on scooter so we're pretty used to long trips on two wheels. If we can ride for 1h30, stop for lunch or sightseeing and then continue for another hour and a half - that's great for us! Most definitely not too exhausting.

Regarding visiting on different times - we could also do that, but we will only be living in Florence for a limited time and can't really take weeks off (my husband is doing a fellowship here) so I do want to try and combine a few trips if they're in the same area :)

We might also just spend three nights in Pitigliano and stop on the way there in Montepulciano for a morning stroll and lunch, actually!

okay, wear a helmet, lol! I can see the island thing, but on Tuscan back roads, it's more difficult to imagine.
Here is the amazing place we stayed in Pitigliano:
https://www.airbnb.com/rooms/10797877?source_impression_id=p3_1619027989_2HP%2Bpm%2BnKVECWaBG&guests=1&adults=1
Lovely owner, gorgeous apartment right in middle of town with view of the gorge from roof deck.
Here is a little bit about the via cave, which we found endlessly entertaining:
http://www.grandvoyageitaly.com/piazza/strange-places-in-italy-vie-cave-the-etruscan-cave-roads-of-tuscany

Florence >Montepulciano spend a night or 2.

Montepulciano pack a lunch and vino head to

https://thevalemagazine.com/2019/07/20/cascate-del-mulino-hot-springs-in-saturnia-italy/

Then on to Pitigliano.

Travel time less than 1 1/2 hours between.

Pitigliano is pretty quiet. I would think 1-2 nights there and more in Montepulciano. You’re right thar Pitigliano is beautiful at night. We stayed at an agriturismo SW of Pitigliano and went to a city overlook in the evenings to enjoy the amazing view. Are you also planning to go to the hot spring at Saturnia? It is about 20 miles from Pitigliano. The natural hot spring is spectacular.

You can stop in San Gimignano on the way to Pitigliano in Grosetto. There's also a Pitigliano in Perugia.

We spent three nights in Montepulciano during summer of 2019. I would recommend at least one full day. We also day tripped to Cortona and Pienza, on separate days so few half days would also be good.

We were there about 12 years ago when it was not quite so discovered. We loved it. We stayed at the first link and enjoyed the 2nd, the third provides good information. We ate at the last place which was sort of an "experience" but truly the food was delicious and the group was so interesting.

https://www.osteriadelborgo.it/ https://www.contucci.it/en/ http://sedimentality.com/welcome-to-montepulciano/ https://www.acquacheta.eu/

A coincidence: the main drag of our neighbourhood includes a pro-level photography-graphic business run by a couple. Their current window display features a pair of his oversized shots of Pitigliano, one cliff townscape plus an alley at night.
I am done. The tuscan.

Your weekend trip sounds delightful. It’s been quite a few years since I’ve been to Pitigliano, but Montepulciano is one of my favorite places to visit. I was there in 2019 and was supposed to return in 2020, but sadly covid happened. I am already planning my return this fall!

I would suggest enjoying the weekend in Montepulciano and not trying to fit another destination in. There is so much to see and do in town and also the surrounding countryside. There are a large number of wineries to visit, cheese tastings, and scenery to enjoy. If you did want to fit in another little town, Pienza is only 15-20 minutes from Montepulciano and is nice to spends a few hours in.

If you are looking for a place to stay, I would suggest an excellent B&B right outside of town called Fonte Martino (www.fontemartino.com). If you want to stay in town, I would suggest Charming Homes (www.charminghomemontepulciano.com).

Have a wonderful weekend exploring – I am very jealous! -Norman