First family vacation in Italy, itinerary help

If you haven’t already- watch and read on this site applicable posts/itinerary ideas/shows on the areas you’ll be in. I’d also recommend the guide book if you don’t have it as things like trains and transfers are covered.

Personally, with that travel group and such a fast paced trip I’d stick to the cities just know what day trips are easy in case you want to do more in the moment. Flexibility and ability to add or remove plans will help flex depending on how you all feel during vacation and what your mood is.

Hi and welcome to the forum!

First things first?

We are staying 4 nights/5 days in Positano. 3 nights/4 days in
Florence and 3 nights/4 days in Rome.

4 nights realistically gives you 3.5 days, tops, depending on when your flight gets in. 3 nights will realistically give you 2.5 days in Florence, and 3 nights will give you 2.5 days in Rome. What you're not figuring in here is the packing up, checking out, getting to the train station (or bus or however you're getting to your destination), sitting on transport, finding your new accommodation, and getting checked in, settled and acclimated to your new surroundings. It takes more time that you might think! :O)

Before getting into tour or day-trip stuff - and even without tours there will be attractions you're going to want to order timed-entry advance tickets to - it would be best if you as a family spent some time with some guidebooks to determine what you wish to see and do. Honesty, I don't think you have time for day trips from Florence but it depends on how MUCH of Florence is of interest to you.

Pompeii is more easily done from Sorrento or even Salerno, and I'd honestly have chosen Sorrento over Positano with your teenagers along; it's bigger and offers more tourist amenities in early spring INCLUDING ferry service at least to Capri and Naples. The boats may not be running along the coast from Positano at all in late March ( they usually start right around April 1) but I don't know if the start date for 2023 has been determined yet.

https://www.positano.com/en/ferry-schedule

Teens should list their top three sites they wish to see. Forget "best"--you all should choose what is of interest to you.
I am not getting the day allotment--I count in nights but only so I understand how many whole days I have. Travel days are often a time suck--going to and from train stations, checking in and out, etc.

Pompeii is a difficult day trip from Positano. You might consider a different base--many choose Sorrento, though that is very different, but it what I would probably choose if planning on visiting Pompeii. Tell us more about your kids--I assume most would find Naples much more interesting but it depends.
Are you all outdoorsy? I would only put that many days on the coast if you plan on doing hikes (will be too cold for water sports).

Once again Kathy offers excellent advice. Go back and do a day-by-day itinerary of just the logistics of moving from one place to another. You'll find you don't have as much time as you think you do. You will lose a full day's worth of time just getting to and from Florence.

Sinc you're flying into Naples and out of Rome, I have a radical idea of skipping Florence altogether. That will give you more time in the Rome/Naples area. Often when trying to see too much, you end up actually not seeing anything.

Sit down as a family and study guidebooks and watch lots of YouTube videos. Then, triage your must-see sites and then fit them in the time you have.

yikes, you all make valid points...i am not thinking about the last day would be really pack up and traveling. We get into Naples at 2pm (Italy time) Our driver will be there waiting for us to take us to our villa in Positano. For that part of the trip...its really more about just enjoying the scenery, relaxation, and just taking it all in. We don't have many plans other than cooking class in our villa, if weather permits boat ride to Capri, and taking the bus to see a few towns. Its low season there, so will be very low key, but that is what we wanted.

My kids are kinda all over the board. They definitely love the outdoors, history, food...and really just excited about going more than anything. Our thoughts were maybe seeing Pompeii on our way back to Naples Train Station. The driver bringing us to the train would be able to bring us to Pompeii and then to train station if we wanted. Then the train to Florence and take a taxi to the hotel. Then after Florence take the train to Rome, where we then will take a taxi to the apartment.

Pompeii with the driver would be the way to do it, but it depends on what time you need to be on the train.

... if weather permits boat ride to Capri

Weather is another reason to stay in Sorrento. If it's yucky out, you can hop the cheap Circumvesuviana train to Naples for a day of inside activities, including the excellent archeological museum where a lot of the treasures from Pompeii and Herculaneum reside. There really isn't much at all to do in Positano, and it'll be too cold for water activities. And again, the ferries may not be running from there at all in late March so you'd need to go to Sorrento to catch a boat which does run in the colder months.

And again, Pompeii is right along the route between Sorrento and Naples.

I personally wouldn't advise the Cinque Terre from Florence; it's another highly weather-dependent location, too cold for the beaches (such as they are), no fun in rain, and a lot of train hopping to get around. It's better if you can stay there a night or two. While I think you'd be shorting the riches of things to see in Florence if you do a day trip at all, Lucca or Siena would be easier. Your teens could rent bikes and ride the city walls at Lucca, weather permitting.