Hi KMG, A few years back my family took a Tuscany tour with Roberto Bechi that Christine mentioned above. We enjoyed it, but we were staying in Siena not Florence. We signed up for one of his joinable tours but we were the only ones so in essence it was a private tour. Lots of fun and we saw lots of Tuscany countryside. Last spring three of us stayed in Florence and wanted to do daytrip to Siena and San Gimignano. I had seen an interview that Rick Steves had done with Anna Piperatto and went with the agency she coordinated with in Florence called Tours in Tuscany. They arranged a private driver, a private walking tour in Siena with Anna Piperato, who is an art historian, professor and Rick Steves guide in Siena Siena tours with Anna and then the driver took us to San Gimignano and we explored that on our own. The driver then returned us to our hotel in Florence. It was a full day. Not cheap but we divided the cost three ways. Very enjoyable. Our driver spoke English, provided us with lots of info, and day went well. Tours in Tuscany also offers their own tours so check those as well.