Naples, Sorrento and Positano

Overall it sounds reasonable, a couple of comments:

A visit to pompeii could be coupled with heading back into Naples to see the Arch. Museum and maybe lunch (the pizza you know)

The 27th seems hectic. It seemed to me that getting around on the coast was time consuming, slow boats, slow buses, slow trains, waiting for connections....trying to get to Capri may take a few hours, plus working with the schedule on boats back to Naples may leave little time on Capri, plus hauling your bags with you. Not sying don't do it, just really look into the connections to get to capri and when you need to head to naples. It might make sense to add time to Sorrento and Day trip to Capri from there.

Why do you need to spend the last night in Naples? I wouldn't haul my luggage to visit Capri. Just go back to Positano, then on the 28th depart from there. It's not that you have to catch an early flight from Naples. There are trains to Rome every 30 minutes.

What about staying in Positano first? You can do Positano and the rest of the Amalfi coast the first 3 days. Then head on to Sorrento. And you can easily do Capri and Pompeii has day trips from Sorrento. You don't need to spend the night in Naples just because you have a train in the morning. You can also easily do the Amalfi towns as day trips from Sorrento. Although I do understand wanting to maximize time in Positano!

I did a similar trip last year and loved that part of Italy. All except Naples … I feel like if you visit Naples, you get a bit of street cred. Naples is one of those cities you love or hate. I was on the "hate" end. We went for two reasons - the pizza and the archaeology museum. The pizza was great but not any better than any approved Neapolitan restaurant I've been to anywhere in the world. The Archaeology Museum was fine - I did not need to spend a night in Naples to see it though. I found Naples to be rough and chaotic and pretty sketchy.

We stayed a few night in Ischia and if you have time to stay a night there, it might be worth it. We chose Ischia over Capri and fell in love with the island.

We stayed in Sorrento at Rosita B&B for 5 nights. You can do of above from Sorrento and not haul bags around. Everything takes time in Italy so making connections with bags and checking in, you are spending way to much time moving around. Positano is good but Revello is better. You can do the coast towns easy from Sorrento, as well as Capri, Pompeii. Skip Naples unless you have more time.

We loved Naples and split our trip between it and Sorrento (with day trip to Amalfi). My notes are here: http://enclosuretakerefuge.com/2014/06/05/a-study-in-steps-petraio-in-naples/ AND here: http://enclosuretakerefuge.com/2014/06/07/in-amalfi/.

We stayed in Sorrento, because of access to the train to Pompeii and Herculaneum (as well as Naples and Rome). As writers note, every morning, the line there for the Positano bus was longer than would fit on the "next" bus. Rick's book notes that if you are visiting the Amalifi coast by bus, see Positano in the morning, because when you get on the bus in Amalfi in the afternoon to come back to Sorrento, the bus won't even stop in Positano: It's too full from Amalfi.

I also found Positano a tiny bit disappointing. It has glamor, but also crowded street-corridors jammed with stores on both sides, and hundreds of steps, to get to a small, stony, crowded beach. I'm glad we didn't sleep there. (Opinion.) If you haven't been to Barcelonetta, Sitges, Bodrum, Split, Rovinj, Ostend .... maybe you'll enjoy another beach resort. We also made a considered decision to skip Capri for the same reasons. Also, we'd seen a blue grotto in Croatia, and everyone says the Capri grotto takes a huge amount of time to be processed by a tourism "machine".

I also fell on the "hate" side of Naples. The pizza was good, and inexpensive, but not actually better than other sources in Italy, or even in the U.S., when fresh mozzarella and tomatoes are used. We waited 25 minutes in line to have lunch at Pizzeria Gino Sorbillo (which had a poster suggesting they now have a branch at the port ... ) The Archaeology Museum is excellent. I had trouble finding some of the chapels clearly noted on Rick's map.

I think the "fear and threat" factor in Naples is greatly overrated. Yes, someone is always trying to sell you a service, but I never felt like I was about to be abducted. We stayed at the higher-end Palazzo Decumani, a gut-renovation in an excellent location, with fierce air-conditioning and big rooms. A healthy walk from both the Arch. Museum and the main train station.

I am not sure about all of your itineraries, but much can be accomplished I think staying in Sorrento. The more we travel, the more we come to like staying in one place and day tripping in and out. The bus to Positano didn't appeal and we took a beautiful boatride back and forth instead. Pompeii is very easy as a daytrip from Sorrento which is served by bus, train and boat. Capri can be easily done, though we did not. The town itself is lovely, ideal for relaxed strolling and evening activities. We spent four nights in October and loved it. Unless you want to see Naples, you can easily just wake up in Sorrento and be be back in Rome easily. Have a great time whatever you do. The region is beautiful, the fried sardines are ethereal, Limoncello beats gelato, and Pompeii and Herculaneum are extraordinary.

I'm in general agreement with what others have said, but will add my voice so as to emphasize a few points. We found Positano so uninteresting that, after a couple of hours, which included having lunch, we left. It's mostly one shop after another peddling clothes and tourist stuff; and, as someone else said, the beach isn't very attractive. Just as a side note: we took the Emerald Grotto tour, since it leaves from Positano. DON'T! It's one of the worst tourist traps imagineable. You can visit Capri as a day trip from Sorrento. Get an early start, and be sure to check the time of the last boat back. It's pretty early - - 6ish is what I remember. We liked Anacapri better than Capri town. I don't see where you've allotted any time to seeing Sorrento. It's certainly worth a day, as are Ravello and Amalfi each.