Just 2 quick thoughts:

1. Take 1 day from CT and add it to Rome.
2. Drop the car in Orvieto and train to Rome from there.

Too many days in CT, three nights will give you two full days to complete the hike from town to town. From driving that route, I don't remember anything too scenic about the trip. Add that day to Rome or Venice.

We did a trip similar to yours a few years ago when my kids were your kids' ages and they were bored to tears in beautiful Tuscany. Also didn't really care for Cinque Terre, but my mistake was planning it mid-summer when it was very crowded and hot.

IF you want to keep your original itinerary though, I'd skip Cinque Terre, and train from Venice to Florence, which will take just under 3 hours. Spend a night or two in Florence with a side trip to Pisa ( kids will love seeing it up close, even though it's tourist central.)

You could also arrange a bus trip to one of the medieval hill towns.

Then pick up a car and drive to Tuscany.

Drop the car, train from Florence to Rome ( about an hour and a half on the Eurostar).

About Pompeii: It's an exhausting side trip from Rome. The drive there and back is around 6 hours.

IF you would consider a totally different itinerary, I'd highly recommend flying Venice-Naples, then spending some time in Naples, Sorrento, and the AMalfi Coast.

Of all the trips we've taken to Italy ( and we've taken quite a few) this was the favorite one for our family.

To get back to Rome, you simply take the fast train from Naples ( only 90 minutes). It's very easy.

This was/is the favorite Italian trip for our family. Kids are now 24 and 21, and they still

Sorry that my post got cut-off! Lastly, if you are going to Italy in the summer months, try to plan and book your trip as soon as you can. Planes/hotels get booked months ahead.

Wow, thank you for the quick replies. I appreciate the ideas to shorten the Cinque Terre leg...and will look into the Venice Naples Sorrento Amalfi Coast itinerary. When I was 13ish, my parents dragged us through France and Italy with a eurailpass and no plans for accommodations anywhere until we got to the city, bags in tow. It was a strangely wonderful trip that I still remember -- and Pompeii and Pisa (and Venice and of course Rome) were my favorite memories from that trip; we went to Napoli but I don't remember it.

I'm planning this for June, if it works out. I've found nice apartments (or hotels w/ family rooms) in each locale still available, with budget in mind, but realize I need to reserve quick.

But flights are still so high for that time, and the thought of waiting til one month before to buy tickets (for the best prices) is nerve wracking. Right now June flights are $1400 open jaw (PHL-VCE, FCO-PHL) -- but end of Feb flights are just under $1000... Any idea whether waiting til May will be too late for June flights?

I'm also planning a BIG birthday. (I just can't get myself to write out those two symbols yet. ) Husband is suggesting Paris, I am kind of leaning Italy but I wish I knew where to go as nothing is really sticking out as THE PLACE!

Enjoy YOUR trip and happy planning!

Don't wait until May! You may find little or no availability for your dates. There used to be fare sales sometimes in mid-late winter, but I think those are a thing of the past. Unfortunately, $1400 per person is about right for the summer months. Leaving and returning midweek is sometimes a few dollars cheaper per person.

February is off-season for Europe. That's why you're seeing lower fares right now.

A final note about Pompeii: It's only 30 minutes from Sorrento on the local train, or about 20 minutes by car from Naples, though you might want to take a taxi since the driving there is pretty crazy!

Pompeii is interesting but Ostia Antica is much closer to Rome, more to see, and easier to get to for a day trip. I've been to both and highly recommend Ostia Antica. I downloaded a podcast from Rick Steves that directed me around and I had a fabulous time, including a stop for lunch at their cafe.
You'll definitely want to add a day to Rome. My favorite city
There are free walking tours of the historic district that leave every evening from the Keats/Shelley house at the bottom of the Spanish Steps.
Book a tour guide for the Roman Forum otherwise it's a confusing mess of ruins. Beautiful but confusing.
I did a day bus trip from Florence to Siena and San Gimignano. Much better than driving. Got to see the countryside as we drove and had time for lunch in Siena before continuing to San G.
There are similar day trips to Pisa, wine tours, vespa drives thru Tuscany, etc. It's easier to unpack and stay in one place and do day trips than to keep packing up and changing hotels.
Get a video or guide book and ask your kids what they'd like to see.

$1400 is good for June. If the flights are what you want, I'd grab them. Sometimes there are sales in late winter, but it's rare to snag a deal any later than that--and it's rare to get much less for Italy anyway. In addition to monitoring flights on Kayak, I check every airline that flies from my airport individually--sometimes sales pop up on their websites that will not appear on a consolidator website. good luck!

I just want to emphasize my agreement with two suggestions already made:

1) Transfer a day from the Cinque Terre to Rome.
2) Substitute Ostia Antica for Pompeii for your "day trip" from Rome. Easy, simple, cheap, wonderful.