Itinerary advice please.

I would definitely FLY into and out of Sicily. I don't know what you were referring to regarding "public transportation" as Sicily is an Island, and it IS possible to catch a ferry or something, but it will be a very long trip. You can book one way TO Sicily, either into Catania or Palermo, depending on where your tour starts. and fly back home also from either Catania or Palermo again depending on where your tour ends. I use Alitalia. Lots of daily flights, and they're more 'generous' regarding your luggage/weight than say a Ryanair, but lots of people love them. There aren't many direct flights from Naples. Flights from Sicily also usually they go through Rome. Alitalia and Delta are partners. If you're using DAL to get to and from Italy, they may be able to add these flights on and save you a few $$. Just make sure you either spend the night before the tour in Sicily or get a very early flight, as weather, etc., can cause a delay or cancellation.

Hi,
You can take the train from Sicily to the mainland. I took it from Taormina to Naples. It is a pretty long ride, with nice scenery here and there. They are regional trains, not the LeFrecce fast trains so they are not as nice or comfortable and slooow. I would fly into Sicily if possible. Easyjet, Vueling and Ryan Air are low cost carriers that can connect you there from Rome.

main,

A few thoughts on your questions.....

• Day 5 - one of the easiest locations to pick up a rental car is Orvieto (Umbria), as it's only about an hour outside Rome and the rental agencies are close to the station. Note that for driving in Italy, EACH driver will require the compulsory International Driver's Permit, which is used in conjunction with your home D.L. You'll also have to be vigilant to avoid the dreaded ZTL (limited traffic) areas which are prevalent in many Italian towns, as hefty fines will result if you pass through them. You may find it helpful to have a look at THIS website.
• Day 13 - it would be easy to drop the car in Orvieto and then travel by train to the Amalfi Coast. The details will depend on which town you plan to stay in. Sorrento is one of the best locations to use as a "home base" in that area, as it has rail transportation. It's easy to travel from there to Naples, Pompeii or other locations. Positano is only accessible by Bus, car or boat. Which town to use as a base will depend to some extent on which places you plan to visit in that area.
• Day 21 - your best bet to get to Sicily is probably to take a short flight from Naples Airport (I haven't checked which airlines operate on that route, but Alitalia is likely one). You can easily get from Sorrento to Naples Airport via the Curreri Viaggi bus (about an hour). You can check the flights at http://www.whichbudget.com/ or http://www.skyscanner.com/
• Day 31 - again, a flight is the quickest and most efficient way to get back to Rome. The flight options will depend on which city you depart from (Palermo, Catania etc.). I'd recommend returning to Rome the day prior to your return flight to the U.S.

An easy place to pick up a rental car before Cortona is Chiusi train station. You need not return the car to the same city; Orvieto is another option on the train line, where the same agency may have offices. Try www.autoeurope.com for a price quote.

Ravello is not a great location for public transportation. You'd always have to take a separate bus down the hill to Amalfi before connecting with bus or ferry along the coast. Sorrento is a more convenient transport base for going various directions, so that you wouldn't have to stay in Naples.

For overnight ferries from Naples to Palermo, see http://www.gnv.it/en/ferries-destinations/palermo-ferries-sicily.html.

If you are signed up for a Rick Steves' Tour, you can get a personal travel consultation for half price.

From the Amalfi Coast area, you can take a ferry from Naples to Palermo, or a flight from Naples to Palermo or Catania (depending on which is more convenient for the start of your tour; Catania is a larger airport and gets more flights). I'd fly; look on Skyscanner for all your options: http://www.skyscanner.com/. There's no need to go to Rome to get to Sicily if you're already in or near Naples.

For your transatlantic flights, see if you can get an open jaw ("multi city") itinerary, into Rome and out of Sicily, all on one ticket. This makes things much easier. If you can't, you will need to fly back to Rome the day before you fly from Rome to the US to ensure you don't miss the connection. Fortunately, there are lots of flights between Rome and the Sicily airports. I used Alitalia, which has the advantage of including one checked bag in the regular fare, so it can actually be cheaper than the "budget" airlines. If you do want to use Alitalia, book as soon as you know your dates to get the cheapest tickets (which sell out fast), and use their "International" website rather than their US one, to get the best prices offered.

Weather can affect where you go or how much you can do in a day. When are you going?

The national train system is Trenitalia. Their trains go to Naples and Salerno. If you want to visit Pompeii and/or Herculaneum, it's most convenient to take the local Circumvesuviana train that runs between Naples and Sorrento. For the rest, you'll use buses and ferries.

Try to book your flights open-jaw, into Rome and out of Palermo. That way, with the Palermo flight included, if there are any flight delays from Palermo, your airline is bound to adjust your flights. If you book an independent flight and there's a delay or a schedule change or if your luggage gets misplaced, you're on your own. If you have to but separate tickets, then I highly recommend spending a night in whichever city you fly home from.