Perche

Better. Fewer places means more time at each. For example, you now have 4 nights in Florence. That's one too many for me when the Amalfi Coast beckons, but it's a personal choice. With 4 days in Florence it affords a day trip to Pisa, or San Gimignano, or Siena. Pisa is the easiest, so it depends a little on how comfortable you are with trains. Do it the on day 3 of your stay if there for four days, to break things up. I wouldn't do it if you go to Florence for 3 days.

Same principle in Rome. After 2 days, might be nice to get out of town, away from the crowds, into a smaller, quieter town, breaking up the stay. Don't go to Orvieto first. Do it on the 3rd day, if at all. Leave in the morning, back to Rome in the evening. You can decide when you get there.

You list Pompeii as day 12. You can't spend the whole day there, especially in July. It's too hot, too crowded, and you'll have had your fill after a few hours with a guide. This is a half day including travel time, then figure out where you are going to go to spend the night. I'd just go back to Naples.

It's just a short train ride back and forth, but in July, this is when I'd recommend a car service. I've hired a taxi to take me from Naples to Pompeii, wait for me for 3 hours, then take me back to Naples for 75 euros, but that was in the off-season. I've also taken the train from Naples to Pompeii, but in the summer that's a tough ride and I wouldn't. It's hot, packed, and not air-conditioned. Your itinerary should say Pompeii/something, because Pompeii in July cannot consume the whole day. You'll need a guide, and with back and forth, it's only half a day from the time you leave your hotel until the time you get back.

I really suggest you go back to Naples. You don't want to check out of your hotel and bring your luggage to Pompeii. I mean, you can leave it in the trunk of your driver, where the heat will probably reach 175F. Pompeii also has a place where they make you check in your stuff because your not allowed to bring stuff into the ruins, so what are you going to do with your stuff?

In this context, I wouldn't get separated from my stuff in Pompeii. It will be a much nicer experience if you just leave it all in your hotel, go downstairs, get into an air-conditioned car, avoid the crowds, have a guide explain things to you, then go back to the car and be back in Naples where your stuff is safe in your hotel room, then have a leisurely dinner to cap off a memorable day in Naples. It's not a whole day trip. Your driver won't wait all day. Half a day

Day 13 you have Sorrento/Capri. This suggests you are going to sleep in Capri that night? I wouldn't, but it depends on your budget. It is better at night, but wow, it's expensive.

If you're in Naples and you've already been to Pompeii and are then going to next stay in Positano, there's no reason to go to Sorrento. Sorrento is a place to bed down for day trips. It has little intrinsic value of its own. It's a cruise ship port, one of the most touristy in all of Italy. It's great if you want to use it as a base and day trip Naples, day trip Pompeii, day trip Positano, day trip Capri because its centrally located. But it isn't a place to visit.

From Naples you can get on the high speed boat to Capri in the morning, and to Positano that same afternoon. Now, you have the evening of the 13th in Positano, and the whole 14th and 15th in Positano to play around with.

I think that one problem is that you are mixing up "where to stay," with "itinerary." They are different. For example, to over-simplify, possible places to stay are; Florence 4 nights; Rome 6 nights; Naples 3 nights; Positano 3 nights. That's it. That's the first thing to decide, then secure your hotel rooms in those places. Then decide on your itinerary. You'll be really glad that you're not doing a bunch of packing and unpacking every other day.

Then, having secured the hotels, fill out the itinerary. e.g., Florence 1st day walk around, start dealing with jet lag, eat something light that PWMTrav recommends (Mercato Centrale) and get to bed. Day 2, Duomo, Ponte, Arno. Day 3 Siena/San Gimi/Pisa day trip. Day 4 Uffizi.

Don't forget that Florence is Florence for a reason. It would be a mistake to miss a sunset from Piazza Michelangelo for a day trip to San Gimi. Really, you only have four days in Florence. Do you really think it is so empty of things to do that you'll be bored and need to fill in the time with day trips?

I think you won't be, but I understand a half-day trip to see one other place like Siena. Just don't miss Florence because you're too busy planning day trips. You have no idea how many people who've said they've been to Rome, they were there for 2 days, but they never scratched the surface.

After Florence, just get to Rome. Again, hotel planning comes before itinerary planning. Once you have your hotel in Rome you can decide what you want to do there. Day trip to Civita di Bagnoreggio? No problem. You can look up the train schedule the day before. Orvieto instead? No problem. There are frequent trains. Go to Termini. Missed one? Catch the next one.

Then it seems that you want to visit Naples. That's another, "I'll miss this train and take the next." As long as you already have a place to stay. Once you have a place to stay, then you can figure out what you want to do, e.g., "Lets make reservations do a half-day trip to Pompeii!" Lets see the Veiled Christ. Let's go to the archeological museum where most of the artifacts from Pompeii are, before we go there! Let's get ferry tickets to stop at Capri on the way to Positano!"

Once you get to Positano, relax, and that's the end of it. Once you are there, you can decide, "Let's go to the beach!" Or, "Let's go to Ravello!" After all, if you want to go to Ravello from Positano, it's just a matter of walking to the bus stop. I think the fare is about 2 euro (I would visit Amalfi over Ravello). Or, you might just say, "We're tired. Let's just go down to the beach, and after sunset, we'll open up that bottle of wine."

I think you shouldn't worry so much about the itinerary, and figure out where you want to be, then get the hotels. Once ensconced in Florence you can decide, "Let's take a day trip to Pisa." Or not. It can be a spur of the moment thing. Just decide where you are staying.

(This was written on a dying cell phone with a broken screen from being dropped on the pavement last week in Venice, so not spell or error checked because some parts of the screen won't work.)