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@s1mon
Very jealous of your trip, a couple of years ago I rode through Tuscany and it was one of the most glorious parts of my European trip. Such beautiful scenery, fantastic roads, slightly less crazy driving than nearer the coast, and food to die for.
I travelled across the country and two of the most enjoyable roads I found have Siena in the middle! The SR222 from outside Florence to Siena and the SR438 from Siena travelling SW. The SR222 is a lovely hilly road, passing through the Chianti region, fantastic vineyards and lovely villages, quite a few coaches due to the proximity to the most tourist saturated cities in the world but once you are a few miles away it feels like a different more tranquil and real part of Tuscany.
Siena itself is a really great city to wander and I can't wait for the opportunity to go back.
The other route that sticks in my memory follows the SS438 which cuts through beautiful farmland and follows a ridge that climbs to give the most awesome views of vinyards and farms all around. The roads passes through Asciano, a perfect Tuscan village with really very good food, You can then wiggle your way to Sinalunga and climb up to the hilltop town of Montepulciano, (about 70km from Siena) drink fabulous wine then probably do the same route back as its so lovely!
Enjoy your time there UG!