I've posted a couple of questions in the course of working out this itinerary, but I just wanted to post the whole thing and see if anyone had suggestions, comments, etc. In particular, restaurant suggestions would be nice, although I have some already, and I'm sure I can find tons more by searching this forum.

Oct 22, Sat (Fiesole, Villa Aurora)
Arrive FLR 9am from PHL. Taxi to Villa Aurora in Fiesole. Walk around Fiesole. Early dinner, early bed (but not so early that we miss the sunset!)

Oct 23, Sun (Florence, Olga's House)
Morning bus or taxi to Florence. Drop bags or even check in if our room is ready. Take train to Lucca, have lunch, walk around. Depending on the time, take train onwards to Pisa. Return to Florence for dinner.

Oct 24-26, Mon-Wed (Florence, Olga's House)
Meet brother and SIL Monday morning. Explore Florence.

Oct 27, Thur (Montalcino, La Crociona)
Pick up car in Florence as soon as possible. Hopefully on the road by 9:30am. Leisurely drive through Chianti. Arrive La Crociona early evening, for a four night stay. Dinner nearby (Taverna dei Barbi, maybe?), maybe an after dinner walk up to Montalcino.

Any suggestions on one or two quintessential Chianti hill towns to stop in?

Oct 28, Fri (Montalcino, La Crociona)
Visit Sant'Antimo first thing in the morning, then drive to Montepulciano. Stop at Pienza, and any small interesting towns on the way (Bagno Vignoni? Monticchiello? San Quirico?)

Oct 29, Sat (Montalcino, La Crociona)
Visit Montalcino, Monte Oliveto Maggiore, maybe a vineyard or two near our agritormiso, depending on when we get back to base. Is Asciano worth stopping at this day? What about the little towns between Pienza and Asciano (Trequanda, Castelmuzio, etc). We also might switch the abbies (Sant'Antimo this day, Monte Oliveto Maggiore Fri)

Oct 30, Sun (Montalcino, La Crociona)
Siena all day, probably stay for dinner, although we may want to avoid driving after dinner.

Oct 31, Mon (Venice, Locanda Correr)
Drive Montalcino to San Gimi. lunch and brief visit in San Gimi. (maybe a morning stop in Monteriggioni?) Return car in Florence, late afternoon train to Venice. OR drive straight from San Gimi to Venice and return car there. I've heard people say that in Italy there are not excessive one-way fees for car rentals. Is that true? If we drive, I gather it is about 3.5 hours? Would it be worth stopping somewhere (Padua?) for dinner?

Nov 1-3, Tues-Thur (Venice, Loconda Correr)
Explore Venice.

Leave early Friday morning back to USA.

I know we still need to do some planning for Florence/Venice. Also, can anyone see a way to squeeze a trip to Volterra into this itinerary, or would that require too crazy of a day?

I have to admit that I have not looked at your itinerary as closely as I might have, but if you don't get to Volterra, please do not spend too much time regretting the fact. The entire town is built of a dark grey, oppressive stone; within an hour or two, it starts to weigh on you. The only work worth looking at in the Archeological Museum is a statue called "Ombra della Sera." You do not, I promise you, need to look at 500 Etruscan burial caskets. And I'm normally an art-history freak...

What is not to like ?
You have done your homework and it will be a great trip.
BUON VIAGGIO !

Hi ms,

Good plans.

I would drop the car off in Venice.

Restaurant in Florence:
Il Ritrovo Via dei Pucci 4/A 055.281688 Best food for the price Has fish. Full dinner w/wine abt 40E pp Closed Monday
From Pzza San Giovani (NW corner of the Pza del Duomo) walk one blk East to Via dei Martelli. Go left to Via dei Pucci. Turn Right. Look very carefully on left. No sign. Door could be locked. Ring bell.

Also see my trip report for some others in florence and Venice.

http://www.fodors.com/forums/threads...p;tid=34451044

Just back from a wonderful driving tour of Umbria and Tuscany. Two comments/answers on your itinerary:

==if the only reason to go back to Florence is to return the car, try to save yourself the hassle, and take the autostrade to Venice. Not exactly a relaxing drive, given the traffic, but you'll be there quicker. Dealing with the "major" rental firms directly, it seemed difficult to set up different pick-up and drop-off points. However, going through autoeurope.com I got a great deal, and had no problem or extra expense in picking up in Venice and dropping in Verona.

==some suggestions for your trip through Chianti. First, visit Radda in Chianti, as nice, small, well preserved town in the heart of the region. Nearby is Volpaia, which is worth the short diversion. Volpaia is a beautiful little village visible from Radda. You can get an excellent lunch at Osteria Volpaia. Second, another great lunch candidate is Osteria del Castello, in Brolio, on the grounds of the castle (closed Thursday).