Chianti Drive: Siena or San Gimignano first?
 

I only have a day to visit Siena and San Gimignano with a private driver. All the bus tours seem to be going to Siena first then San Gimignano. Would any of you recommended flipping it (base in Florence) to avoid the bus crowds? Or is it so crowded in July that its really not going to matter? Is going to Siena first more scenic?

Also any places I must stop by that is between these places for some great scenic pics?

It's going to be crowded in both but less so very early in the morning and very late in the afternoon, so you might think about starting out as early as possible. Then, decide where you want to have lunch (and/or dinner if you're going to make it a long day).

In terms of possible stops along the way, were you going to ask the driver to take secondary roads, or do you want to reach Siena/SG as quickly as possible on the autostrada?

We are not in a huge hurry to get to those places. Would prefer scenic route if that is what the secondary roads are. He is going to plan wine/ olive oil tasting and lunch at San Donato in Poggio. How early is early? He suggested a 9 am pick up from our hotel.

It seems your driver is also your guide. I would take his advice on timing and where to go first. (I'd want to leave earlier, but you might be charged for that.)

You'll see lots of beautiful scenery everywhere. Highway SR222 (Via Chiantigiana) goes through the heart of Chianti and is one of the iconic drives in Italy. Hopefully, you'll be on this road for part of the day.

Thanks Jean. He seems pretty flexible and willing to customize as we go along. I'll mention it.