I was emailing off and on with the owner, Luca, for months, and even cancelled some of the specific day trips from time to time, but he was patient and... read more simply changed what I asked.
My wife and I used Hills and Roads for two straight days, and both days we were driven by the very personable and handsome Cristiano (easy ladies, he's married). On the first day he took us to where we wanted to go, which was San Gimignano and Siena. He pointed things out to us along the way, then dropped us off at the front gate of San Gimignano. Even though I did research ahead of time and knew what I wanted to do, Cristiano was very helpful in telling us where to go and what to do to have the best experience. We set a time with him to meet him back at the front gate and when we got there he was waiting for us.
On the way to Siena he made a quick stop off at an old walled city that he thought we'd like. He first took us across the road for a great photo opportunity in a field, before dropping us off at the front of town. It was a very small town and wouldn't take long to explore so Cristiano told us he'd just wait down the hill and look for us to come out. Sure enough, as soon as we got to the road he drove up to get us.
He then took us to Siena and walked with us down to il Campo to explain the layout of everything. He told us to walk down a street he pointed out, when we were done exploring, and he's be waiting there. And once again there he was to open the van door for us.
The next day we needed him to take us to Cinque Terre from Florence and he was a few minutes early again, loaded our bags, and then off we went. We stopped at Pisa on the way, where he explained about the town and the tower before dropping us off in front of where the tower is. About 45 minutes or so we came out and there he was again waiting for us. When we got over the insane up and down hills in Cinque Terre he dropped us off right at the front of our hotel, we settled the bill (he was very intent on making sure we agreed on how many hours we used him), and then dropped our bags at the front door.
He answered a lot of questions about not only history, but what it's like to live in Italy, and anything else you can think of. I even asked him about a certain type of tree I kept seeing and he knew all about that.
Bottom line, there's no way I'm personally driving around Italy, and some places like Siena and San Gimignano can't be reached easily by train. For about 350 euros or so you get someone to take all of the stress away, and it is so worth it. And don't forget to tip him when it's over. For two days we gave him 50 euros total.