Now roast MY itinerary

Looks fine! You have been validated.

One question- what time is your flight out of Naples? Make sure you can get to the airport easily that morning. If it's a flight before noon I would stay in Naples that last night.

It will almost certainly be really hot in Pompeii in July. What time will you be able to start your exploration there if you are arriving from Florence? Would you be able to get there substantially earlier if you traveled there from Sorrento? I think Pompeii would be more enjoyable if you could get an earlier start. (Unless, that is, you expect to arrive late enough that it will be cooling off during part if your visit.)

OK...thank you for asking, and that is a concern. Originally I thought we should be in Naples the night before, but any nice area is a 40 minute drive to the airport, and Hotel Anitche Mura in Sorrento tells us they can get us to the Naples airport in under an hour. So, with not that much of a difference, I am opting to stay in Sorrento for one more night. We will leave Sorrento at around 6:30 AM, our flight is at 9:55. I hope the universe in on our side.

We will leave Sorrento at around 6:30 AM, our flight is at 9:55. I hope the universe in on our side.

I do too.
Is that flight going direct to US? or somewhere else in Europe?
I'd probably leave Sorrento 5:30-6. Just a bit more wiggle room.

One question?

Why no Venice?

Only 2.5 hours train ride from Florence.

Validated!
for your 7/7-7/11 stay in Sorrento...you mean Sorrento Base to explore the whole Amalfi coast and Sorrento right? AND did you make time for some Pizza in Naples, I know it is so cliche, but it is the supposed birthplace of Pizza and seriously a totally different pizza experience that what we are used to. We are so happy we made the opportunity to experience true Neapolitan pizza en-route to Sorrento.

You are using Naples only as a point to travel through on your way somewhere else, but you aren't staying there? Rather than leave at the crack of dawn to get to the airport from Sorrento and hope that nothing goes wrong, why not stay in Naples the day before your flight. We really enjoyed our time there on our RS tour last year.

Venice was originally on our list, but I realized something had to go, so it was Venice that got cut, as we were pretty set on going to the Amalfi Coast. I have always wanted to visit Pompeii and Capri, so Sorrento seemed to be a perfect spot. Using Mondo guides, we are stopping at Pompeii on our way there, Next day tour of the Amalfi Coast, third day a boat excursion to Capri, using Rick Steve's "shared tours". I hope we are not overbooked, but I tried to keep our itinerary at one tour/activity per day.

Next trip to Italy I will get to Venice, Cinque Terra, and the Dolomites!

We will leave Sorrento at around 6:30 AM, our flight is at 9:55. I hope the universe in on our side.

That is leaving no fudge factor and assumes the outbound flight is to a Schengen destination.

Making a plan that requires all of creation to be on your side to be successful requires a degree of optimism greater than I possess.

Yes, I am not usually optimistic, but I don't want to take a way a day from our trip traveling to Naples and staying near the airport, where there is nothing to see or do. The hotel concierge seemed to think it was all very doable. I have a back up reservation in Naples if we change our mind. We have a room booked at Palazzo Alabardieri in Naples, which looks lovely...but is still a 45 minute ride to the airport.

Naples is less than 20 minutes to the airport, likely even faster at that hour when there is no traffic.
I understand not wanting to cut Sorrento short, but Naples is a blast--if you get nervous about the early ride to the airport.

I am actually very nervous about it. 20 minutes would have swayed me, but that's not what they said at the hotel in Naples. Maybe they are being extra cautious? And we're not being cautious enough!

I was thinking that we could change the itinerary a bit: check out of our hotel in Sorrento on July 10 and go to Pompeii on that day--and then to Naples, staying overnight in Naples before our flight. I tend to think that is the best course of action, but my husband and the hotel concierge are convincing with their counter arguments.

That's a conundrum, I just know from my closer hotel it was ten minutes, with few other cars on the road. So, I mapped it for your hotel to be sure it was not considerably further. At that hour with a prebooked taxi, 20 minutes should be fine. I would choose that over an hour in a car because I just hate morning in general. Good luck!

https://www.google.com/maps/dir/Palazzo+Alabardieri/Naples+International+Airport+(NAP),+Viale+Fulco+Ruffo+di+Calabria,+Naples,+Metropolitan+City+of+Naples,+Italy/@40.8601577,14.2331052,13z/data=!4m16!4m15!1m5!1m1!1s0x133b0855308f75bf:0x4438f90ef9f7644d!2m2!1d14.2414145!2d40.8347844!1m5!1m1!1s0x133ba81e8986d9e3:0xbf48c58ba6c9356d!2m2!1d14.289243!2d40.8847493!3e0!4e1!5i2

3 routes from Palazzo Alabardieri to the airport. 17-20 minutes ( taxi)

The 40 minutes trip is via transit.

And where that flight goes does determine how early you need to be there.

I think your itinerary is fantastic. Well done!

Our flight is Naples to Newark. Luckily, no international connection. Thanks to all of you for sage advice!

Then you should be there 3 hours preflight
I’d stay in Naples

We stayed in a hotel with our RS tour that was very near the Spanish Quarter in Naples. It took us about 15-20 minutes to get to the airport by taxi.

It looks great. We have been to Italy 3 times and we still haven't made it to Venice. Next time!

Your hotel is 4.6 miles from the airport. Should take 15-20 minutes. Be there 2 1/2-3 hours before. It’s a very small airport.

I’m going to agree with everyone that said that you should stay in Naples the night before. If your flight is shortly before 10 AM, you were supposed to be at the airport three hours before that, which means that you need to get there by 7 AM. If you leave Sorrento at 6:30 AM, you will not make it in time.

Obviously, this is your trip and you can do what you like, but all of us are speaking from experience when we say that the best plan is to hope for the best, but plan for the worst. There are many things that can happen in the morning and missing that flight could cause a lot of problems.

Yes, I do agree. I am going to tweak our itinerary, and it might work out for the best anyway. Thank you!

Your itinerary looks fine. Just be prepared for some nasty heat. We were in that area in mid June 10 years ago and it was stifling. We are going to northern Italy starting in Rome this coming June July. Hopefully the weather won’t be as warm as last summer. Air conditioning will be our friend. Enjoy your travels.

I am going to be a contrarian here - I’m not sure why a lot of folks here keep insisting on airport arrival 3 hours ahead of departure. There is always some element of risk in all travel but if not checking bags, and doing online checking via an app I have found 90 minutes more than sufficient.

As long as you weigh the risk appropriately, I would spend the last night in Sorrento. You have ample time without having to leave at 6 or 6:30.

All six of us are checking bags. I wish we could be the family that didn’t. I’m working on it!

Wait, 6 checked bags plus cabin items? You'll need to make sure that your hired drivers can take all of that.

Yes, 6 checked bags! We have a driver that can accommodate, set up by the hotel in Sorrento. Probably another reason to get to Naples the night before.

probably another reason to get to Naples the night before

I'd say the opposite. With that much to lug around, you want to minimize the number of times you change hotels. And you'd need 2 cabs to get from a Naples hotel to the airport.
So, best to wake up very early and leave from Sorrento to the airport.

I think your itinerary looks great. I also think staying in Sorrento is the way to go, just leave at 6 instead of 6:30.

Looking forward to OP's July 15 entry on how what they choose works out.