My wife and I in our 70's, in the mid portion of our ~8 weeks itinerary (after visiting Ljubljana and Bled for 3 nights, Venice overnight then boat the eastern Adriatic for 7 nights, stay in Venice for 3 nights, train to Verona for 4 nights and train to Ravenna for 2 nights) by early September, my wife and I will have 5 nights in Florence in an airBB.
I'm certain we may be road weary and want to just stay put in our apartment in Florence. have found we can easily plan enough to fill all of our days and nights staying put in Florence and may elect to forgo day trips either to Siena or Luca by train while there.
We then Leave Florence by car to Radda for 2 nights and drive on to Montepulciano for 3 nights before dropping the car in Orvieto where we will overnight before training on to Rome 5 night and flying onwards to Israel.
Is a day trip to Siena after leaving Radda by car to our next stop in Montepulciano a reasonable plan albeit limited in time?
At what time of evening would you suggest we leave Siena for our drive further to our next base, Montepulciano?
My concern is darkness on an unfamiliar road.
Thank you for your consideration.
S