Suggestions on sightseeing itinerary
 

My fiancee and I will be on our honeymoon in mid August 2015. We'll be arriving midday 22 and departing on the 24th. I've been to Florence before but she hasn't. I've hired a private driver for the 23rd and wanted some suggestion what to go see.

She definitely wants to go see Pisa and, of course, the countryside around Siena. I was thinking we would go from Florence to Pisa and see the tower and then head down to Siena for sightseeing and lunch at a winery.

I know this will be about 4 hours in a car but I'm trying to make the most of our time and mitigating lost time with the private driver. Ideas? Should we skip something the day with the private driver and something else the afternoon before/after?

Thanks!

I am aware most will disagree with the amount of time but it's what we scheduled and we're trying to make the most of it while still trying to relax.

If I understand correctly..you get there on 22 and leave a mere 1.5 day later? And you want to see 3 places???
Especially for your girlfriend that has not been to Florence before, you need to stay there. Forget the private driver (seriously) as well as Pisa and Siena. Florence is better seen walking.

I agree. It will go not well, cramming in three cities to see by car. Pisa isn't even worth driving to. It's not famous because it's beautiful, it's just famous for being famous because the tower leans, like hundreds of other leaning towers in Italy. If you happen to be driving past and can see the Tower from the highway without having to get off, you can roll down the window and take a picture, but that's it. It's not worth a four hour drive. Siena is beautiful, but that means you'll have to skip experiencing Florence, especially if you want to explore the countryside as well. This is the usual trap of thinking Italian cities can be seen in one or two days to take pictures, and not to experience what a place has to offer.

For a day and a half, bag the side trips and do the historic center of Florence. If you want a tour operator to do something like a walking tour of the city - food or art - I can recommend someone. That might help with skipping lines to the major galleries and such.

Or hell, I'll tell you where to sit around and drink wine and eat too much food if you prefer that.

But maximizing the experience, IMHO, means staying in Florence. The city was a part of my honeymoon as well, according to my wife the best part. I'd say do 2 nights at Hotel Lungarno, kick around Oltrarno for a day, do the galleries the other day.