Would love input on two-part Italian itinerary

Two nights in Cinque Terre is fine.
But what time does the flight leave from Rome?
One thing I don't like about this is the amount of checking in and out of hotels.

The flight home from Rome leaves on the morning of May 9.

The part with the family is fine if those are the things everyone wants to do, but there simply is no time for either Florence or Rome here. I would pick one or the other. I didn't go to Rome till my 4th trip to Italy; focusing on fewer things I think gives a better experience. You do need to be in Rome the night before, you might consider staying at the airport Hilton and making it easier on yourself We did that once when flying back from Barcelona, with a Rome flight the next morning (we had added the side trip at the last minute) We took the train from the airport into Trastevere and had a lovely dinner under the stars and then headed back to the airport for the night and were there for our flight. Florence is dense with Renaissance artistic sights; wonderful place and takes time. I wouldn't want fewer than 3 full days/4 nights in Rome either. A day for the Vatican and two for historic Rome.

May 1 is the most important holiday outside Christmas and New Years in Europe. Expect many things to be closed. On our very first trip to Venice 35 years ago we arrived unknowingly on May 1 and even the boats were not running; we had to walk from the train station with our giant old fashioned, non wheeled suitcases, over a mile to our hotel -- over bridges every few steps. I think it isn't quite as bad now, but don't assume anything will be open that day unless you confirm it.

I appreciate that information about May 1. Fortunately, we will still be at our agriturismo in Tuscany that day, so it will probably be a good day to hang around there and enjoy the activities on the property. I am hearing the comments about choosing Florence or Rome at the end and not trying to do both.

I know you'll have a great time overall no matter what, Catherine. But it's far from a 'linear' trip!

That being said, the only tweak I'd make, seeing your restrictions and the fact that you're flying out of Rome for home, is to bypass Florence on the way back from Monterosso, and spend 4 full nights in Rome, just barely enough time to get a feel of the vibe in one of the greatest cities on the planet. When you leave the C.T. on that day, you'll have a short 25 min train ride from Monterosso to La Spezia, then transfer to a Freccia train to Roma Termini station, just under 4 hours. Not the worst.

Getting back to the Sorrento part...and jet lag (which I experience as well and am sympathetic to)...if you wanted to try to get there the first day (hate that dead day in Rome!), and assuming that most flights from the Midwest or East Coast arrive at Roma Fiumicino in the morning, I'd take a taxi (regulated at 48 Euro I think) from the airport to Termini, take the Freccia train (1 hr 7 min) to Naples Centrale, at which point a private driver can meet you when you get off the train & take you directly to your hotel in Sorrento. Your hotel can set that up for you--they do it all the time. That won't be cheap, however--cost us 95 Euro last March--but in this scenario you could be borderline brain-dead and still make it happen. And you'll be there, won't have to get up the next morning in Rome and pack up all over again.

That will give you 4 nights in Sorrento to sanely do everything in daytrips--Naples, Pompei, Positano, Amalfi--with Sorrento (especially if you're staying near the bus/train station) being such a great base of operations--all those destinations are an hour away at most, maybe a few minutes more for Amalfi.

Enjoy your planning!

Skipping Florence after The Cinque Terre in order to eliminate one more check-in/checkout is a good idea. But, could you flip The Cinque Terre and San Cassiano instead?

28th-1st Cinque Terre
2nd-4th Whole Family in San Cassiano.
5th You and husband remain in San Cassiano picking up a day trip to Florence.
6th-9th Rome

It would mean two separate car rentals or letting the car sit wasted in a lot outside the Cinque Terre. But you could rent a smaller car for the southern portion of your trip and something larger for the Tuscan portion.

Based on the helpful comments on the forum, I've made some changes to our itinerary, so now it looks like this. The dates are nights.

April 24-27 Sorrento (Amalfi Coast) Now when we land in Rome on the morning of the 24th, we will go straight to Sorrento rather than spending one night in Rome.

April 28-May 1 Tuscany

May 2-May 5 Florence (When I polled my kids, it turned out they all preferred to move to a city, not the CT, after time in the country. The trip from out agriturismo in Florence to the city proper will take only an hour or so.)

My husband and I have to be in Rome the night of May 8 to fly home early on May 9. So we still have to decide where to spend the nights of May 6 and 7: Florence, which would give us nearly six full days there, or Rome, which would mean about 3.5 days in Florence and 2.5 in Rome. One factor I'm thinking about is that one of the days in question is a Monday and it looks like more things are closed on Mondays in Florence than in Rome. Thoughts?