We were staying in Florence for several days and wanted to spend one full day in Tuscany. We hired a driver recommened in other tripadvisor posts -- Alessandro Cammilli -- and we were very happy with him. Our itinerary started in Florence at our hotel and then a drive up to San Miniato al Monte Church (in Oltrarno, up a big hill past the Pitti Palace) with a great view overlooking Florence. From there we drove to San Gimignano (hiking up a tower for a great view) and got there early, before it became too crowded. Next, we drove to Siena. The Piazza del Campo, where the Palio is held, is spectacular, as is the Cathedral of Siena, and we highly recommend visiting it. As we were drving toward the chianti wineries, we made a quick stop att the castle at Monteriggioni, which was great, then headed for a great lunch at a place recommended by Ale in Panzano -- Dario Doc. The restaurant is above Dario's butcher shop and is wonderfully off the beaten path but perfect. Finally, we stopped at two wineries for wine, olive oil and balsamic vinegar tastings.
Rather than try to figure this all out by ourself, we at first considered renting a car or going by train and bus, but aafter checking all pur options, we realized we needed a driver so we could see the countryside and visit the wineries without any concers. Our choice was Alessandro Cammilli and we were very happy with him. He picked us at 9:30 am and dropped us back at our hotel around 6:00 pm and all his recommendations were spot on. This was a great day and one of the absolute highlights of our trip.