TeeGirl:

Looks GREAT!

Oaktown Traveler

LOL AGAIN, Oaktown!

I'm not sure about dropping the car off in Venice - it is a very long drive, and in my limited experience it costs A LOT of money to pick up/drop off in different Italian cities. But I agree with the rest of the posters - this is a much better schedule. But you do realize - you are staying in three Tuscan towns, not two: Florence, Siena, and Cortona. As for your driving plans, Lucca works better with Pisa than San Gimignano. S.Gimignano is a natural on your way from Florence to Siena. Montalcino, Pienza, and Montepulciano are all close to each other (but don't be crazy - just visit two in one day). I've never been to Cortona but it looks like just the place to base a quick drive through Umbria. And as for Venice, go straight from the train station to a vaporetto (ask your hotel for the right one) and enjoy a jaw-dropping boat trip up the Grand Canal. Congratulations.

TeeGirl:

Just logged on...just like I told you:
All Gone!

My Best,
Oaktwon Traveler

<<in my limited experience it costs A LOT of money to pick up/drop off in different Italian cities>>

Never heard of this, and never experienced in plenty of car rental experiences in Italy.