Your plan looks pretty good. I like it. Here are a few comments.

Don't stay in Ravello. It's got a beautiful view, but it is kind of isolated, and getting in and out to visit other places wastes a lot of time. Positano of Amalfi are a toss-up.

There is no problem dropping off a rental car at Fumicino before the office opens. However, if you concerned, check the web site carefully or call hertz to make sure.

On the other hand, driving in Italy, even in in the wee hours of the morning, can be an adventure. Lots of highway construction and other unexpected obstructions. Leave yourselves plenty of time...

Your plan looks quite sensible. Just one thing to think about - if you don't like moving hotels every couple days you can do the entire Naples-Pompeii-Sorrento-Amalfi Coast from one base location. We spent 8 nights in Sorrento and did day trips to Naples one day, Pompeii another, Capri, and a few to the various AC towns. In that part of the country the getting there is definitely part of the fun and doing it without luggage is great. We took buses to Positano/ Amalfi/Ravello, buses or boats back. Took train to Naples, boat back, etc. It was nice to get back to the same hotel each night and not do a lot of checking-in, hauling bags. Nothing wrong with your plan, just a thought.

Here's my trip report and link to photos: http://www.fodors.com/community/europe/amalfi-coast-rome-and-croatia-images-of-three-hot-but-wonderful-weeks.cfm

I don't like moving around that much. I would take the Curreri bus from Naples airport to Sorrento and stay 4 nights Sorrento and 4 nights Amalfi or Positano. You can day trip to Naples one day from Sorrento.

I would consider making a day trip to Ischia from Naples, instead of Capri from Sorrento. Capri has a very tourist-trodden feel about it, Ischia, while busy also, feels more Italian to me.

I would return the car and spend the last night in Florence and taxi to the airport (10 minutes) the morning of your flight. You would be taking a huge risk trying to drive from southern Tuscany to the airport to catch a 7:00am flight- don't do it.

I didn't notice you were flying out of Florence. I agree with Zoecat that you might want to spend the last night near the airport in Florence. I have no experience flying out of this airport.

You guys/gals are fantastic!!! Every point is well taken. I thank you all. I'm going to look into all your comments and suggestions. I will look into all of them, and amend accordingly. I will post again after some more reserach.
Can't thank you all enough. -HH

Incredible! Isabel, I just read part of your link to your last trip report! So informative and insightful. Thank you. I will need to read it again carefully again. May print it out for future reference.

Having taken most of your guys' suggestions, I think we will skip staying in Naples, go directly to Sorrento there for 4 or 5 nights, and spend the last 3 nights in Positano or AC in a room with a view so we won't have to go back and forth too much along the AC. I will look into the hotel that Isabel stayed in. If others have suggestions about Sorrento or AC hotels, I'd love to have them. Mostly looking for spacious clean well apppointed rooms at convenient/good location, 3 stars...maybe 4, but not necessary. All my gratidute for your postings...HH

Here is an old thread that may help.
http://www.fodors.com/community/europe/bob-is-back-from-the-ac-with-pics-to-prove-it.cfm

This is very much like the first trip I took to Italy in May of 2004 except we did it in reverse. We started in Florence, then to the Cinque Terre for 2 nights, back to Tuscany for 5 nights. Then we trekked down to Ravello and stayed there for 4 nights. It was heaven on earth.

I loved staying in Ravello ... it was a bit out of the way but it was glorious and not overrun with tourists. We day tripped to Capri (meh..) and Positano. One morning we hopped the bus to Amalfi early in the morning and it turned out to be the daily school bus as well. The kids in Ravello go to school in Amalfi - and the day we were on the bus, they were all studying for an English test. It was so much fun listening to these school age kids practicing English while we barely spoke a word of Italian.

Your trip sound blissful and I hope you have a wonderful time.

I can almost guarantee that you will love this hotel if you decide to stay in Amalfi, which would be my location of choice.

http://www.hotelfloridiana.it/en/index.asp

Go a lot was there in May basically looks
fine but my wife and I enjoyed.

www.hoteldelfino.com GREAT views over Capri(www.otel.com $80)

Majestic Palace Sorrentp was a great hotel to visit Pompeii

from 5 minutes away on the train penthouse suite $100 for us

Bast Wester Paistea sea view $120 AARP/expedia.com nice

Amalfi very vertical pretty cliffs no island views hard

to get around but nice...

So a few days in each location...

Naples pretty dodgy ok not great we always minimize

our time there for prettier less dirty places.

Tuscany looks great!

Have fun!

Book the Best Western Hotel Pasitea from C$100.79 ... Expedia Guest Rating. 80%. ... “Hotel in Positano IT” Best Western Hotel Pasitea located in Positano Italy was very ...

www.expedia.ca/Amalfi-Coast-Hotels-Best-Western-Hotel-Pasitea.h...

Surrounded by orange trees and lush gardens, Majestic Palace boasts wonderful views of Mount Vesuvius and Capri. Catch the train to the centre of Sorrento in just 2 ...

www.booking.com/hotel/it/majesticpalace.en.html

Just a zip by train to Pompeii then Naples

2 minutes to downtown Sorrento for 2 euro SITA bus to

Positano Amalfi coast... older Brit Hotel at great price point

QuoVadis: It sounds like you've never been to Amalfi. The town is not at all vertical; the walking is flat in the center, with an incline so slight as to be imperceptible along the main street as it approaches the hills.

I, for one, am getting very tired of your incessant shilling for the Hotel Delfino. Not only is this hotel not in Sorrento proper, but the rates you post ad infinitum, are non-existent to anyone but yourself. Please take care to read the original poster's query before posting.