Too rushed. If you are flying out of Rome, put it at the end instead of staying there twice.

I think you need to use resources to get facts on travel time.

For train segment, use http://www.fsitaliane.it/. For driving you can you google maps, for example. You probably know that google map travel time estimate is rather optimistic. If the driving time is tight according to google map, you surely cannot do it in reality.

It is not difficult to estimate how much time you have left at the destinations. On the day you move, you need time to 1. pack your luggage, 2. check out/settle bills 3. travel to station/pack car 4. travel to destination 5. park and unpack car/travel from station to hotel 6. check in 7. unpack your luggage.

You can quickly figure out that staying in Rome twice penalizes you with the second set of overhead time. See if you can land in Rome earlier or land in Florence instead in a multi-city itinerary.

Also, do not attempt to approach Florence unless you have a firm grasp on ZTL (Zona a Traffico Limitato) unless you don't mind paying traffic fines that can approach or even exceed 4 digit figures.

Include the Tivoli gardens if you're going to Rome. They are quite unforgettable. If you're going to Pompei, also go to Herculaneum, much smaller and more intimate, very close and much better preserved.

Moved some things around and going to do the following:

Train from Rome to Florence on Sat
Florence Sun / Mon
Montalcino Mon - Wed
Rome Wed-Sun

In Rome, I know the question has been asked, but can I do Capri and Pompeii in one day, since it is summer?

I think you wouldn't do either site justice. There are great day trips out of Rome and you should consider Ostia Antica rather than Pompeii. Very close to Rome and many say, the best preserved. Maybe give some thought to Tivoli for Villa d'Este and Hadrian's Villa.

Your itinerary has so much travel in it and you will end up feeling rushed and exhausted. In an effort to see as much as possible, you will end up seeing less than you think (except the inside of trains and train stations). I know it's tempting to cram too much in but resist that temptation. And it will be hot!,

After reading your reply, denisea, I think we are leaning more towards 3 nights in Montalcino, 4 nights in Rome. Skipping Florence all together. I have been to Florence, Bologna, Venice, Rome before. My wife has never been to Italy.

Worst case - we can visit Florence via train from Rome if we wrap up Rome early.

ckg,

Much better plan. Let your wife enjoy her first visit to Italy. I, personally, would not try to make Pompeii or Capri at day trip. It's just too far and long of travel time.

You will return!

Buon viaggio!

Each to his own!
You can do Pompeii and Sorrento in a day from Rome, or do Capri and Sorrento in a day from Rome, but it may be difficult to do both Pompeii and Capri in a day from Rome.

Do your research on train schedule and boat schedule, then decide if it is doable. You'll need a minimum of 2 hours at the Pompeii site.

Since I need a car in Montalcino and am coming from Rome - where is the best place to rent / return?
I hear horror stories about renting/returning Roma Termini.

Doing the Amalfi area from Rome as a day trip is a VERY long day.

If you want to do Capri and Pompeii you would want to get the earliest train out (6 am?) to Naples and from there take the ferry or hydrofoil to Capri - where you would have several hours and a rushed lunch. Then take the ferry back to Naples and the local train to Pompeii where you could rush around for a couple of hours before collapsing. (Be aware the sight is VERY hot in the summer - and to really see much you need 5 hours or so). Then you could have a quick dinner in Naples and take a late train back to Rome. Frankly I would rather put a sharp stick in my eye - esp in August when you can expect temps in the high 90s, lots of humidity and incredible mobs of other vacationers.

ckg,

I trained to Chiusi, picked up a rental there and drove to Montalcino for 3 nts. Orvieto is another easy rental location. Check to make sure these smaller town offices are open for what you plan.

Also confirm that the company you are renting from is close to the train station. I believe the Hertz rental company is the office just a short block from the Orvieto station. The office near the Chiusi station I have not used. At the time of my trip the rental office location required a taxi ride, but there is one close by the station.

Good luck with it. I have found that even in one city, I can't see everything! I think you will enjoy so much more (know it sounds crazy), if you don't try to cram in too much. I wish you all the best in planning your trip and hope it all goes perfectly.

Thanks everyone for the help! I was able to get a car in Chiusi, stay in Montalcino, and have a tour guide for Rome. Now, only if the weather will cooperate!