Dear Aks,
The itinerary Valentina proposes is doable but keep in mind it focuses on you dashing through the countryside with the goal of seeing as much as possible to take photographs, not really to stop and enjoy each place you visit. As long as you're fine with that, then the itinerary will work out fine.
Some tips to make the driving and stopping for photographs "stress-free":
- roads in Tuscany and Valdorcia are all two lane and curvy. Italian drivers like to pretend they are on a race track and like to go fast - slow down and let them pass you (they'll pass you even on curves as long as they have some space). It also gives you more room to have time to stop on the spur of a moment to take some photographs.
- the roads don't often have banks on the side where you can stop, but there are a lot of houses and farms with access off the main road into which you can turn into and stop... you can walk back a little way to get your shots.
- some of the best photographs are not taken from the main road... so take small detours and head onto unpaved roads and get out and walk a little ways in (without trespassing, of course). Some of the best shots in chianti: park in the village, then walk out of the village, take shots of the medieval towers and vineyards all around from a higher vantage point.
- lastly, remember to stay flexible with your schedule and enjoy each stop along the way!

and buy a good road map of Tuscany before setting out, or bring along/rent a GPS!
Hope you have fun on your trip

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