Interesting perspective. For the general good I must say that Florence is one of the greatest tourist cities in the world (some say its the best). Pisa would rate as one of my least favorite cities, although the Tower and surrounding square is certainly worthy of a short visit. As to wine tasting, our favorite area is the S222 road which runs between Florence and Siena and runs through the heart of the Chianti district. There are other great wine areas such as near Montepulciano. A private driver should be able to take you to some wineries and also make a stop in Pisa. If the private tour companies do not show this as an option, do not hesitate to e-mail them your request and ask for a suggested itinerary. If you have no clue who to e-mail try sending an e-mail to Francesco at email@example.com
. He runs a local rental car company but is also very willing to provide a driver. Also keep in mind that the so-called Tuscan countryside is a very large area and cruise passengers need to focus on the region that would form a triangle with Livorno, Florence and Siena at the points. Of course its also possible to take a train up to Lucca for the day or even drive (private guide or rental car) to the Cinque Terre region (this is what we are doing on May 1 during a cruise stop). I would also urge you to reconsider a visit to Florence. It does not have to be a hectic visit with the tiring museums, but can simply be a relaxing day just strolling the streets, shopping, eating a long lunch at an outdoor cafe, etc. It would just leave you wanting to return again and again. Going to Florence is an affordable day (pretty cheap if you use the trains) but hiring a private car/driver will most likely cost you $400. Have to run now. We are in FTL and are boarding the Grand Princess in a couple of hours for its 20 day cruise to Rome (somebody has to do it).