Two women, Italy mid-october.

I like Andrea's itinerary and as both she and ekc said, not enough time in Venice or Rome. Ordinarily I would suggest dropping a couple of days in Tuscany, but because of your timing, I agree with ekc to drop the CT. Weather by then is very iffy. When it's sunny, it's a gem. If it's cloudy, not so much, and if it's raining, it's a total loss. Save it for next time. Once you've been to Italy, there will be a next time!

Your destinations are good, but in my opinion are out of order. First, remember that 2 nights in a location is only one full day there. Okay, I would go in this order - Venice, Florence, CT, traveling by train. Train from CT to Pisa and pick up car. Tuscany by car. Drop car in Orvieto, then train to Rome. Have a great trip!

How about staying in Siena instead of San Gimignano. You can rent a car in Siena just for the days you need it. Siena have more restaurants and places to go for the evenings.

I have to agree with Siena. We stayed at Agriturismo Marciano and it was one of the highlights of our 3 week trip. They offer optional dinners some nights that are not to be missed. I would not want to stay IN Siena with a car, but Marciano is just outside of town. It was a good location to take day trips from.
Check out their website and read reviews on Trip Advisor. You could pick up your car in Pisa and drop it off in Orvieto. Spend a little time there before heading to Rome.

IMHO, you don't have enough time in either Venice or Rome, unless you have previously spent quite a bit of time in each city. I would drop CT and add a day each to Venice and Rome.

I have to agree that CT would be the place to drop. If you do drop it, go to Florence, spend your time there, then pick up your car at the airport on the way out of town. Use it in Tuscany and return it in Orvieto. Train to Rome. If you drop CT I would add a day each to Venice and Rome.

I would not drop CT from your itinerary as it is the only time you will be by the sea. I love the water and CT is such a unique place and will not be over run by tourists. Even if its cold it is still wonderful to wander around and relax a bit. Yes, you might return but then again you might now... so if you keep CT in the mix you will have seen most of the highlights of Italy. I was totally happy with a few days in Rome as I do not need to explore every nook and cranny...not enough time and more places to see.... its always about choices and you can never do it all. You should be able to have some wonderful days exploring the Tuscan countryside and villages as well as a number of vineyards. I drive all over and did find Siena to be a pain with a car. I love San G and also any number of small places in the countryside. We stayed at Poderi di Archangel and it was great. Also the tiny town of San Donato.. two or three hotels, a church and a vineyard and it was beautiful.

Charlotte, I also feel the Itinerary mentioned by Andrea would be more efficient, and a better one to consider. As you're planning to drive, are you aware of the usual "issues" regarding driving in Italy? If not, post another note for the details. One other question - have you travelled in Italy before, and are you familiar with rail travel? There are a few "caveats" to be aware of. Happy travels!

Having just come from Italy (several days in Tuscany) I'd like to put my 2-cents in and say that Siena would be better than San Gimignano because it is more centrally located. I hope you'll explore my favorite two towns (Montalcino & Montepulciano) but that would be a long haul from San Gimignano. Siena, on the other hand, sits square in the middle of so many wonderful hill towns. Make sure to have a good GPS for driving. It saved us so many squabbles.

Thanks everyone for your very useful suggestions. has anyone used RON in Rome as a planner? He charges $150 for 7 days of question/answer sessions. Thanks!

First of all, I adore Ron In Rome! I was singing his praises and posting links to his website about 30 minutes ago...again... But... if I were you, I'd first ask as many questions as possible on this forum. We're cheap; more bang for the buck. Have the two of you read any guidebooks, watched any travel programs, or have any ideas of exactly what you want to see and do in the locations you've chosen? What types of questions do you have for Ron? They may be pretty simple-to-answer ones... Then after picking our brains, go pick Ron's. And don't forget to really dig into his website for info - your answers may already be there. As far as 'coaching' goes, though, I'm sure he's very good!