Italy...at last! We're planning two weeks Mar 23 - Apr 6.

I need some input on our itinerary. I'm really having a hard time working out how to split up 5 nights in Tuscany.

Areas we'd like to see (but maybe the logistics don't work): Lucca, San G., Volterra, Siena, Montepulciano area, Pienza(?), Cortona. Is there a good (charming) central location from which to visit all those in 5 days?? What "must see" am I leaving out??
We would probably prefer "in town" as opposed to rural accomodation (we're two ladies).

Here's the preliminary itinerary:

Wed: Rome 9am 5 nites
Pensione Panda or apartment

Mon: Train to Orvieto, tour, pick up car
5 nights in Tuscany

Sat: Turn in car, Florence -- 3 nights

Tues: Fly out of Florence

How does that sound for a first trip? Any help with Tuscany will be appreciated!

Jeanne, For that itinerary you will need to train to Chiusi and not Orvieto to get your car. From there, you cannot do all of those from one location--maybe 2 locations. I would stay 3 nites SE near Montepulciano and Pienza and do most of your wish list from there. Look at www.lacosta.it or Palazzo del Capitano in San Quirico.
Then, drive via Siena to near San Gim. for 2 nites--stay at La Cisterna or Antico Pozzo in town. Lucca will be tough, but could be done as you transition to Florence to drop the car--at the airport--do not drive into town. Hope this helps !

Yes, anything helps at this point. Trying to get my head around all the options---to me this is the hardest part of the trip.

That said, I'm beginning to think Lucca and Cortona just don't fit the itinerary. Better to concentrate on one or two locations and see more there.

Re: Chiusi over Orvieto. ViaMichelin says it's only a 30-min. driving difference. I've read so many positive reports on Orvieto...is Chiusi just as good a place to disembark, have lunch and rent car???

So:
Pick up car, drive to Pienza -- 3 nights. See towns along S146. (Work in cortona, if possible)

Leave Pienza, visit Siena, stay in San G.--2 nights. See Volterra from there.

Drive San G. to Florence via Chianti region? Maybe find backroad or interesting place to visit. End up in Florence.

This is getting much clearer.

You can drop in Orvieto but I do not think you can pick up there. The Avis office is across the street from the station in Chiusi and you are :30 from either Montepulciano or, would you believe, Cortona.

Well, that might explain why autoeurope keeps dissing me on the Orvieto pickup!

THAT close to Cortona, huh? Sounds very tempting to pick up in Chiusi around 10 am, head to Cortona, then be in Pienza or Montepulciano area by nightfall.

This is shaping up nicely...thanks Bob!

I picked up a car in Orvieto last month. The Avis office is about a three minute cab ride from the station. BTW, if you're there lunch time, don't miss I Sette Consoli, right on the main street. Sit outside, its terrific.

On the other hand...Bob, this is where your navigating skills come in.

I looked up the routes to do Cortona after picking up the car and it's doable. ViaMichelin says take the Camucia route from Cortona to Montepulciano. But will we regret not driving the lower part of S146 from Chiusi to Montepulciano?

Alternatively, we could go to Montepulciano from chiusi and save cortona for its own day. Drive to Cortona by way of Camucia (SS326), return by way of Sinalunga.

Being the designated "navigator", I would appreciate your input on this.

JeanneB,
In regard to your tuscany part, I would suggest the following.

I wouldn't change hotels during these 5 days and operate from Siena or San Gimignano.
From there, you can visit whatever you want in Tuscany in about an 8o km radius (50 miles?). Lucca, San Gimigniano, Pistoia, Volterra, Montalcino, Massa Marittima, Pisa, and so on.
If you feel like seeing Orvieto, which is a very beautiful town, take your car in Orvieto, visit the town and cover the 120 km to Siena. It is a good plan.