Travel Review: Luxury Italy Vacation, Florence, Cortona, Siena, San Gimignano, Montalcino, Winery, 2-Week Trip

The schedule for visiting Siena and San Gimignano was overwhelming and seemed backwards with mileage to and from. Visit and lunch in Siena was enough especially since San Gimignano was so far out we decided to terminate that plan vs going back through Siena region to get to our hotel. We would have loved to see it, but visiting AFTER Siena and lunch was too much.
Same thing happened at the Winery visits. The furthest winery on Montalcino should have been first and then the other in Montepulciano. I understand that there was a scheduling issue between the 2 wineries. 
If that was the case, one should have been moved to Wednesday which was a free day.