Best of luck on your trip, and I commend my fellow Europe board Fodorites for the helpful and polite advice.

I concur that Munich isn't for this trip. Add days to the places you are most interested in seeing in the plans you already have.

I'd break your proposed itinerary down into 48 hours increments and see how it lays out. To me it looks like this:

Nov 1 - depart US
Nov 2, 3 - arrive Milan & immediately fly to Naples, private transfer to Sorrento w/ stop at Herculaneum, stay in Sorrento
Nov 4, 5 - get from Sorrento to Rom, and stay in Rome
Nov 6, 7 - get from Rome to Siena, stay in Siena, then rent car to explore Siena, Montepulciano, San Gimignano, etc.
Nov 8, 9 - I don't see how you can include Florence &/or Munich with only these "extra" two days squeezed in here
Nov 10 - need to return to Milan
Nov 11 - departing Milan at 11am

Good effort, suze, but that's still a horrible ratio to time in transit vs. time enjoying Italy IMO.

Beware of travelling long distances by car in Italy
 

@ StCirque - Maggiore sounds very interesting - Definitely adding that to our list. :).

Our general advice would be to keep a 30-50 mile radius to wherever you chose to stay in Italy if you are renting a car. Driving in Italy is not the easiest place, and not for the faint hearted in our opinion. The Autostradas (Toll Motorways) are not the easiest to navigate around. Saying that, we absolutely love it too, and would always rent a car, but keep the distances short and sweet and your google maps on! . Whatever you do, you'll have a great time

Good effort, suze, but that's still a horrible ratio to time in transit

Yes I know that :-) I just think it helps when people do their itinerary in that format, a day by day (or night by night even better) list... it helps you see what you are attempting more clearly than writing it out in paragraph form.

Like days 6 & 7 look like doozies! And 8 & 9 just need to be put to what is already on the list, not add more extra stops. My suggestions anyway.

I don't really agree with this. I had no trouble with my initial experiences driving in Italy. Driving on the autostrada is very easy. If you don't want to go fast, just stay to the right. People don't pass you on the right in Europe.

Before leaving, you should familiarize yourself with the international road signs, and with those few particular to Italy. There are numerous internet sites that will illustrate and explain them.

Italy Destination Ideas: Venice and Brescia
 

@bvlenci - We loved driving in Italy, but found that the exits coming straight off the Autostrada took some getting use to.To be honest, it has become part of Italys charm for us now.

We have recently traveled to Venice and Brescia (Lake Garda and Lake Iseo).

For Venice in particular - We'd absolutely recommend the free walking tours

For Brescia - The Cable car on Monte Baldo, and a trip to Lake Iseo is a must

Yes, the turn-offs on an autostrada are very soon after the sign and require you to decelerate very quickly. You need to be alert. But stick to the right is easy.

Unless the OP's itinerary has changed, I don't see any long-distance driving, just a portion of Tuscany.

Anyway, I find driving on the autostrada very easy, esp. if you're using GPS, but I think the autostrade are generally the most dull and boring way of getting around.

FWIW, I don't set a daily driving radius by miles. I measure by time. Thirty miles on the autostrada can normally be driven in about 30 minutes, but on secondary, more interesting and scenic roads, thirty miles could easily take an hour or more and 50 miles could take 2 hours. Considering the OP's limited time and long sightseeing wish list, I don't recommend any long-distance driving.

I usually see warning of upcoming exits beginning about 500 km in advance, or even more. It's less on some other limited access highways.

What I wish they would have is a sign, as soon as you pass an exit, telling you what the next exit is. They have these signs usually just before an exit, for example, you're approaching Loreto and they tell you that Ancona comes next after Loreto. But if you enter at Loreto, you have to wait to find out what's next.

Okay, here is what I understand are your priorities. Your husband really wants to see the Vatican and the Coliseum, you want to see Bavaria, and you are both concerned you might not make it back to Europe. However you also have some stuff planned for south of Rome (Herculaneum, Amalfi) and it is here I am a bit lost, since you also talk of wanting to see Bavaria. Going south of Rome AND going north of it (considerably north of it in the case of Bavaria) even as you are flying into Milan which is not especially close to Munich. This is a big net to cast in a short period of time. By the way AJ Peabody is not kidding, seeing the Vatican and seeing the Coliseum in one day would be hard. With luck, they won't be as crowded in November as they are in other months but they are always popular, they will never be 'relaxed' sightseeing. Try to make it at least 3 nights in Rome if seeing these places is a priority of your husband's.

I am not averse to short fast trips if that is all one can manage - we spent all of 9 nights in Australia as our view was, better some Australia than none - but even we realized we had to be very selective in what we wanted to see. So: There's Bavaria, and there's Munich. Yes, Munich is in Bavaria, but for me (and of course you are not me) Bavaria was about small towns and villages, which of course Munich is not. My point is simply you need to pick that candy in the candy store (to use AJ Peabody's expression) very carefully. Are you sure you would get what you are thinking you will get if you try to fit in Munich?

One thought: If you have enough points to upgrade to business class, you might have enough clout with the airline to renegotiate your air routing especially as November is not high season. Just a thought, it can't hurt to try.