Ok, so here's what seems to be our itinerary. I could NOT (!) have done this without all of your help --You know who you are

Sept 10 - Evening. Arrive Rome (via LAX-Paris-Rome)
Romecabs.com pick us up from airport, drop us off at rental apartment. Over the next few days, possibly Arte di Vaticana Context tour? Lots of sights, eating, drinking & fun.

Sept 14 - Pick up rental car (Kemwel) from Via Veneto, drive up into Tuscany heading to destination in San Quirico, stopping wherever we feel like it. Over the next few days, go on various day trips, ie the Coast, Siena, Cortona, etc....Eat, drink, relax, fun.

Sept. 17 - Leave San Quirico heading up to Florence Airport to drop off rental car. Train or taxi to our B&B in Florence center. A few days of art, shopping, eating & fun.

Sept. 20 - Leave Florence (by train?) for Bologna. Nice budget B&B in city center for our last night in Italia.

Sept. 21 - Get a car ridiculously early in the morning for Bologna Airport for the flight home. (Bologna-Paris-LAX)

The only part I can really comment on is the train? to Bologna. That should be very easy from Florence - I stayed in both places and took the train between them. Check the Trenitalia schedule online to check times, but there should be a lot of direct trains.

Bologna itself didn't exactly charm me, but the food was outstanding, as you'd expect. At least, unlike so many other Italian cities, Bologna didn't feel overrun by the tourists - who were still around but did not dominate a real functioning city. Try if you can to arrive early enough in the day to have two meals there!

Nice trip--you did pay attention.
Have fun--I know that you will. Say hi for me to the old gents at Bar Centrale in SQ--they are a hoot.

Minor detail: There's no train at the Florence airport. You'll go either by taxi or BUS. The bus drops you near the main train station, so then you'll still need to get to your B&B. I recommend taxi, which can take you directly to your B&B.

This looks great! Be sure to visit Pienza, Montepulciano, and drive on some of the "white" roads while in the area.

Have fun!

Is there anyway to get to San Quirico from Rome without using a car? Perhaps a combo of train and bus or train and taxi? I know there are a lot of Italy experts on this site and hope that Pezlie doesn't mind me hijacking this thread with this question. Also where are you staying in San Quirico and in Florence, Pezlie? We are putting together a very similar trip for next spring.

macdogmom
You can bus, but it's not easy. You would probably catch a bus to Montepulciano and change to a bus to Chiusi. Once in Chiusi you can catch the train on to Rome. The problem is the bus schedules can leave you waiting a long time for changes since there aren't that many buses. For bus schedules, check
http://www.sienamobilita.it/EN/orari.html

I believe part of your route would be on LFI and part on Tra-in. One bus schedule on Tra-in that goes thru SQ to Montepulciano is listed on page 16 of this pdf, but there might be additional ones.
http://www.trainspa.it/2009/extraurbano.pdf

Macdogmom, San Quirico is the Palazzo del Capitano (highly recommended by bobthenavigator & highly reviewed on trip advisor) and Florence is Panella's Residence, a B&B that was also highly recommended. The price range for both were very reasonable. Good luck in planning! I will report back about how ours went...

@ Zoecat : The "white roads", huh? Totally new to me! I'll have to look that up...