5 Nights in Tuscany - Help

I can only answer about where to...I would recommend a farmhouse in one of the small towns in the Chianti region. Both Castellina and Greve have some GREAT places to stay and from there it is "easy" to drive to either Sienna or Florence. We stayed at this location last time we were in Tuscany and it is a really nice agriturismo

http://www.agriturismopoggetto.it/home_ing.htm

Air conditioning is essential in August. In fact I would not do without it from June-mid Sept. Certainly you can drop your car off in Rome. The airport is not very convenient if you are staying in Rome. It is less hassle to drop it in Orvieto or Florence and take the train to Rome. I think you'll find 5 night sin one place a blessing. The idea of Chianti is a great one.

I highly recommend staying in Siena! We did 5 days in Siena and 4 in Florence in April, and wished we would have spent more time in Siena. I highly recommend vrbo rental 388386. It was fantastic and very close to the Duomo and some fantastic restaurants. Siena is much cheaper and better for dining, and is just so charming.

When you stay in Siena, I highly recommend Franco Fadda tours if you are looking to do a winery tour. We have done tours in Napa, and this was 10x better. We did the Chianti and Montalpuciani tours and both were amazing.

Lastly, the restaurants recommended in Rick's Tuscany book are outstanding. We haven't eaten at a bad restaurant yet recommended in any Rick Steves book.

We did day trips to Volterra, Pisa, and Lucca. All were fantastic.

Dropping the car in Orvieto is a good idea too. It's only an hour train ride (cheap I think like 9-11 euro). And after you drop your car if your schedule permits you can explore Orvieto for a couple hours. There is a hotel by the train station that you can keep you bags at Albergo Picchio and then take the Funiclare up into town. The duomo there has a nice colorful decorated facade. The town is know for their ceramics. I brought back a couple of serving plates for dinners last time. You can find some nice items to bring back there..

More props for Orvieto as a lovely hill town to visit, on the main train line to Rome, and with handy car rental facilities (Avis, Hertz, others). There's normally no extra charge to pick up and drop the car at any of the vendor's locations in Italy. Try Auto Europe for a price quote.

My choice would be to stay 5 nights in one place and day trip into Florence. It will give a lot of variety to your trip to have the experience of 2 city stays and one smaller town/village. I like Siena but it can be a pain with a car. I would try and find someplace else, or as suggested an agriturismo for a really different experience. I found Florence to be so crowded and hot in the summer (as is Venice & Rome) so a little relief from that would be nice. Just daytrip to Florence.