question about our itinerary

First, have you booked your flights yet? If not, try to fly into Naples and out of Pisa or Genoa. It may cost a bit more, or it may not, but you'll save time and money by not having extra travel to be at your start and end points.

If you use Naples as your base, then Capri, Sorrento, Pompeii and Herculaneum are easy day trips. Further afield to places like Positano or Amalfi are not. That's why the usual advice is to base in Sorrento. The other reason is that some find Naples overwhelming; I liked it. One thing I didn't enjoy was my daytrip from Naples to Sorrento and Positano - these are places to linger, not fly through, so it was a waste of a day.

If you are locked into flying in and out of Rome, you will not need a night in Rome on the way in, but will almost certainly need one on the way out. Getting from the Cinque Terre to FCO will take about 4 hours, and unless you have an unusually late flight, you won't have time to go through security and make your plane if you try to do this all in one day. However, on the way in, you can get a train to Roma Termini and then a train to Napoli Centrale; these trains are very frequent, so there's no need to stay in Rome that night unless you wish to. Getting to Sorrento from Naples requires yet another train (I don't know if the boats are still running in October). If you fly into Naples airport, getting to either Naples or Sorrento is by direct bus, so it's a "one seat ride."

You can get a tour guide if you wish (many do this for Pompeii, for example), but it's not necessary anywhere. In the places you're going, there will be enough English spoken for your needs.

Harold has you on the right track.

We are very experienced travelers; and one of the few places in Italy I have intensely disliked is Naples, because of its dirt and disorganization. Trying to put aside my biases, I still can't see why you would spend 3 nights there, plus the 2 in Sorrento or Amalfi. You can do a day in Naples from Sorrento. Do you have a reason for wanting more? I wouldn't spend 3 days in the CT, either. Your Tuscany time is too short. You need a couple of days, at least, for Florence; then a couple for small towns, which are a totally different experience. Don't worry about language. Any of the areas which get a lot of tourist traffic have lots of English speakers. Also, Italians are very kind and welcoming. They'll do their best to help you surmount any language barriers.

I agree with the previous post. Why spend three nights in Naples? Are there that many things you have researched that you would want to see there? I might spend two extra days in Sorrento/Positano to begin with. If you see Capri that is a day in itself. Or, spend and extra day in the Tuscany Region. Lots of good day trips like to Siena. I might also cut down the Cinque Terre to two days and add a day to Rome. The train service is great and you can see all towns very easy in two days, unless of course you are hiking a lot. I think Rome deserves more time. So much to see. Remember the first day you get there you won't be doing alot because of jet lag tired and time to check into where you are staying. So I might do this:

Rome -4 nights
Sorrento/Positano 3 nights (One day visit coastal towns Amalfi, Ravello, Positano, than one night Capri, than one day Pompeii) left out Naples completely, curious what you want to see there over other places.
Tuscany - Tuscany 3 nights
Cinque Terre - 2 nights

This is not in a particular order but may want to start out in Rome, go to Amalfi area, head to Cinque Terre and than Florence. If you have an early flight you want to stay at a hotel at the airport the night before. Also don't forget this is a tighter schedule than it looks like because of travel time. These are some half day to 3/4 day trips between places here.

Thanks to all of you for your replies...very helpful and insightful. I am going to dig a little more into attractions and revise according to your advice. Will likely be back with more questions in a day or two.

Thank you so much!
Mary-Beth