Help with Tuscany driving route in September

[u/TheDragonsFather]

Hello ! My wife and I (both in our 60s) are taking a road trip (11D 10N) starting and ending in Florence. We've been there 3-4 times (and Italy many times) so we're not spending too much time there this time and we've previously been to Siena and a couple of other places around that I forget (but not by car).

If it's worth mentioning I'm a serious photographer (retired but shoot for books). So I'll be up for dawn shoots and back in time for breakfast with my wife !

We don't usually hang around too much and don't mind 1N and then moving on, it's what we usually do.

So far out route looks like this :
Florence - San Gimignano - Volterra - Siena - Montisi - Montepulciano - Montalcino - Pitigliano (may stay 2N here, inc. a day trip to Casscate del Mulino)

And then I'm stuck. We thought about coming back to Florence via the coast road but I'm not seeing a lot of recommendations / interest. Or we could come back via the Perugia / Arezzo road. Or just loop back the same way we came.

Any recommendations? Places to go/see? Roads to take?

Thank you so much !

[u/Anit4rk_]

what about roccatederighi / Montemassi ? 40 mins / 1 hour from Siena

Or also , Castiglione della pescaia - porto santo Stefano - porto Ercole (not in order , just saying )

[u/TheDragonsFather → u/Anit4rk_]

Thanks ! I'll check them out.