Tuscany Photo Itinerary

I happened to see a new Italian Facebook photo site today. Lots of good scenes I didn't recognize and most had captions noting where they were taken. https://www.facebook.com/ParadisoToscana

Stunning! Thank you for that link

This photographer's website is interesting with examples of photos that work and photos that fail. He includes descriptions and geo coordinates of the locations, and several maps with pins of locations with photos attached. Whether the scenes are more or less well-known is up to you and/or instagram.
https://shirshendusengupta.com/blog/tuscany-italy-ultimate-photography-location-guide-top-instagram-photo-spots-best-places-to-visit

Here are a few of my favorite villages and other attractions, the drive between them is outstanding.

San Quirico d’Orcia, Castiglione d’Orcia, Pitigliano, Bangi San Filippo, San Salvatore Abbey, Radicofani, Acquapendente, Cetona, Sareano.

We always check the website of the Borghi Piu Belli d'Italia (the Most Beautiful Villages of Italy) when visiting an area. The website has a write-up and a gallery of photos for each village. How else would you know to visit the Tuscan town of Montefioralle?
https://borghipiubelliditalia.it/toscana/

Some photograph less well-known places in Tuscany that I suggest Abbey of San Galgano, close to Siena, where you'll also find the real sword in the stone; Natural Park of Migliarino, San Rossore if you're visiting the west side of Tuscany; Bagno Vignoni in the Val d'Orcia; the Vie Cave in the area between Sovana, Sorano, and Pitigliano; the Maremma (especially the Parco Regionale dell'Uccellina). Of course, these are just some examples, as Tuscany is full of characteristic and medieval places to photograph. If you most like history, other Tuscan-related website also suggests medieval places like Monteriggiani, which has a really beautiful castle.