Italy for 9 nights...First time...Please help with itinerary

You ned to get specific about dates - without doing that, it's easy to tell yourself little white lies about how much usable time you rally have. So please post specific dates/times for your arrival and departure days. On a trip as short as yours (and it looks like a very short trip for what you are proposing), just 1 or 2 days (often lost to travel details) makes a huge difference.

First observations...

It makes no sense to travel north from Rome to Florence, then far south (everything else). Your time is very short (maybe too short for what you're proposing), you must keep your routing efficient.

It also makes little sense to stay at two different places (Positano and Sorrento) that are so close together. Pick one.

If (as I suspect) you are flying home from Rome, you need to stay in Rome you last night, so there goes another day.

I have a feeling you are going to need to re-do your plans with just 3 locations, but first post actual dates so folks can help you.

You have only one full day in Rome--is that going to be sufficient for all of those tours?
I would not like moving every two nights, but I acknowledge some like to move more.
Some choose to stop at Pompeii en route to the Amalfi Coast--I'd do that over moving, and I prefer the Amalfi Coast to Sorrento.
If you go to Florence first, you can arrange it so you are in Rome last for your flight out and don't have to travel all day on your last day, but if you have already booked things it may be easier just leave it as is.
It is just as easy to get from Positano to Rome--ferry to Salerno and train to Rome.
enjoy!

Looks like it may be too late as you have booked the tours in Rome at the front end of your trip. The ideal situation would have been to do Rome at the end to facilitate your departure and eliminate one hotel transfer.

Given the situation you describe, I would do Florence last and with your 7PM departure take a morning train from Florence.
Much simpler than to get to Rome from Florence than from Sorrento or anywhere on the Amalfi Coast ( e.g. Positano)

Your schedule for Rome looks brutal.

jtravisano21 - You mentioned you are going to Italy for the first time. It doesn't make sense to spend just 2 days in Rome from the start. Rome deserve at least 4 nights. Florence / Tuscan Villages combined deserve 4 nights. Spend your last night in Rome before departure, that gives you 9 nights. Postpone Sorrento for your next Italy trip. It will be too much of a rush to do 4 locations in 9 nights.

Rome - 4 Nights (June 22 - 25)

Florence / Tuscan Villages - 4 Nights (June 26 - 29)

Rome - 1 Night (June 30 - July 1st)

(Fly Home on day 10)

Way, way too much area to cover in such a short time. Assuming you are arriving from the US, you have one day in Rome before you leave for Florence on the 24th. On the 22nd, you will be a zombie, so your only sightseeing day in Rome is the 23rd.

You get two days in Florence before you leave on the 26th for Positano, which is a haul, and you only have one day there to see the town (the 27th) and then you move to Sorrento on the 28th. If I understand your plan, you then are going to leave Sorrento on the 1st for Rome. Even though you may have enough time to do that, the stress of getting from Sorrento to Naples to Rome would be a deal killer for me.

There is a suggestion to cut down your number of stops, which I will echo. Your current itinerary only spends one day in Rome, and if you plan to do the Vatican tours and the Forum tours in the same day, you will not enjoy the experience much, IMO.

What time does your flight land? Have you booked tours for the 22nd? if so, have you allowed enough time to get through passport control, possibly wait for baggage, get to Rome and to your hotel to check in and drop your bags, then get to the sight for your first tour? Are you taking the effects of jetlag into account?

Rome to Florence is easy. It's probably about 1/2 hour to the train station in Rome, about 1-1/2 hours on the train, then a 10-15 minute walk to your hotel in Florence. But to get from Florence to Positano is a very different story. Fast train to Naples is 3 hours. Then you'd probably take the local Circumvesuviana "CV" train (a metro really) to Sorrento. It takes about 15 minutes to traverse the Naples station, then 1 to 1-1/2 hours on the CV to Sorrento. The CV runs about every 30 minutes, so you may have a long wait in Naples. If you want to go on to Positano, it's another hour on a bus (which may only run every half hour).

Why should you stay in Rome on your last night? A 7 pm flight means you have to be at the airport at 4 pm. Taking the train from Rome needs about an hour. So you have to be at the Rome train station by 3 pm. It's going to take you 1-1/4 hours on the train from Naples to Rome. So you want to be in the Naples station by about 1.30. Remember, 1 to 1-1/2 hours on the CV to Naples - which can run late so you will probably need to allow for extra time in Naples. That means being at the CV station before noon. That doesn't give you time to do anything or go anywhere that day (there's really nothing much to see in Sorrento). What if there's a disruption on the CV or the train line?

If your heart is set on the Amalfi Coast and Pompeii, stay in Salerno. There are fast trains from Florence and to Rome. You can take the train to Pompeii and then a taxi to the ruins. You can get to Positano by bus and ferry. It will make your trip much better and it's an interesting city, beautiful seaside promenade, large sandy beach, and a well-preserved medieval center. I'd still spend the last night in Rome and use the day to see things you'll have missed at the start. I'd also contact the places you booked the tours with to see if it's possible to change the dates.