Capri for 3 nights with teenagers

Suggest you ditch the last night in Capri and return to Rome to spend the last night there. This would be too tight a turn, relying upon ferries, trains, and cabs to all be running on time. What if the seas are choppy? What if the train is late? What if there is a cab strike in Naples? Or Rome?

Voting with wbfey1 here: Capri is not where you want to be on the morning of an international flight from Rome or even Naples, for that matter. As has been mentioned, a bad storm or high winds could cancel ferry service, and you'd want to be much closer to Fiumicino anyway so you have more options in case of a different public-transport snag. I wouldn't stay in Positano that last night either.

Stay in Rome or a Fiumicino hotel on your last evening so you don't have to stress about getting to the airport on time.

I thought you'd decided to skip Capri altogether?

https://community.ricksteves.com/travel-forum/italy/amalfi-and-capri

Another vote for the 'spend the night before your flight in Rome'.

Too many moving parts to try to do it from Capri on the day of the flight

Agree. You are inviting disaster by trying to make it from Capri to your flight in Rome on the day of your flight. Very, very unwise.

For that matter, I'm not sure I'd spend even "2 nights" on Capri at all (not a fan - it's mass tourism at it's worst IMHO, maybe worthwhile for a half-day trip, but not worth doing at all if your trip is short and you skip other, better things to be there), but that's another subject entirely (and tastes vary). But by all means, if your flight departs form Rome, spend your last night in Rome!

Even Positano has non-zero risk for a 12:30PM CHECK-IN at FCO. If you are talking all public transportation (i.e. starting with the overcrowded SITA bus from Positano to Sorrento), it's only slightly less risky than Capri. Last week of May is virtually High Season. We were in Sorrento the last week in May, and every bus TO Amalfi via Positano had more people in line than would fit on the next half-hourly bus. Get my drift?

Capri is indeed attractive, but has difficult topography (including access to sea bathing) and is highly pedestrianized. You are probably underestimating how long it will take to get to Sorrento, where you might spring for a taxi to the train station from the much lower-elevation Marina. It is hard for me to guess whether teenagers would prefer Capri or Positano. Some parents joke that it's all about the Wifi! Personally, I don't like cold sea water and stone pebble beaches very much. But it depends on whether you are from a landlocked place, partly.

You don't mention Pompeii, Herculaneum, or Naples.

You don't mention Pompeii, Herculaneum, or Naples.

Tim, Pompeii was mentioned on one of the OP's previous threads.

We liked Capri BUT, like the Cinque Terre and Venice, it's one of those places best stayed overnight versus day trip to. We had two nights on the island and enjoyed it very much but we spent the peak tourist hours largely away from areas the day-trippers congregated at. Early mornings and evenings were very nice. Did not swim, even though our hotel had a pool.

After Capri we had 3 nights in Sorrento so didn't have to try and get to an airport from there, and wouldn't have risked it.

Thanks for the guidance, will take all of your advice and spent our last night in Rome, and keep capri as a day trip from sorrento if at all possible. We are keeping one whole day to Naples and Pompeii and Vesuvius from sorrento.
This will be our second trip trip to Europe , all these years we have always travelled to USA or places like dubai and Singapore or London, so the kids were eager to try something new like capri as Rome, Florence are agin urban cities I guess .

We are keeping one whole day to Naples and Pompeii and Vesuvius from
sorrento.

IMHO, this is too much for one day. You can probably do Pompeii and Vesuvius but trying to see much of Naples in the time you'd have left over is pushing it. Pompeii will likely be very warm, and it's a huge site that can easily chew up the better part of 1/2 a day or more, depending on how interesting you find it.