Our first trip to Italy

Not sure if your arrangements already require visiting Calabria region. With only two weeks, that visit would be a stretch. If required to go, don't spend much time there. There is a lot more to see on your other stops.

You have too little time in Florence and Rome. Two days is enough in Venice for a minimum visit. Florence needs 3-4 days and Rome 5-6. Sorrento/Pompeii is good for three days.

Rail travel is my preferred method of travel between the cities you mentioned. Driving in Italy is expensive with the high tolls on the autostrada. Distance doesn't require flying.

I suggest you purchase a good guidebook for Italy, Rick Steves has one.

I think the Venice is adequate if you are all organized and ready to do the stuff you want to do in a fairly organized manner. Tricks like buying Doge tickets at the Correr, figuring how to beat the line at San Marco, chaining it together so as not to be too hard on the feet while jet lagged on the first day... doable.
Florence in two days is something I did, and regret. Did not get the Bargello, the Baptistery, the inside of the Duomo, any trips out into the Tuscan countryside... Gotta take a MacArthur on that, but if I could redo that trip, I'd add at least a 3rd day, if not a 4th.
Rome in 3 is short. But if you get a nice taste for it, you can MacArthur it and return someday. I'd try to add a 4th day, if not a 5th.
I don't know anything about Sorrento... so couldn't say, but dropping that lets you add a day to Florence and two to Rome, with one of the Rome days a day trip via train to Pompeii.
Then train down to Calabria from Rome.

I wouldn't drive for this as you are primarily in cities, where cars are more of a liability than a benefit. I would train everywhere.

Jack,

For what it's worth, I think you're trying to pack way too much into such a short period of time. From personal experience, I predict you'll return from Italy feeling like you really didn't see anything and you'll be a little disappointed at how much you spent in order to see the inside of public transportation and hotel lobbies - not to mention the constant unpacking/packing of suitcases.

My advise, for a 14 day trip, pick a maximum of three sightseeing bases and then do some day trips if you feel the need to get out of the city(s) for a bit. Venice, Florence and Rome makes a well balanced and easy to manage 14 day trip. But, if you wish to go to the Amalfi Coast, I would seriously think about eliminating one of the other destinations.

As for the time of year, it's going to be hot. There's a reason Italians try to take the month of August as holiday and head to the nearest beach, Think Florida in August... This also makes places like the Amalfi very expensive and very crowded in August.

If you PM me, I will send you links to my 14 day Italy trip reports.

Work2Travle has given good advice. You are packing in too much even if it wasnàt going to be hot-as-sin out. If the Calabria stop is a must-do, drop Venice (you are not allowing enough time there given jetlag and the wonder of the city). Also, count nights, not days, when planning. It gives a truer picture of time utilization and helps assure you make your reservations correctly as lodgings think in terms of nights, not days. You will not get to see and do as much as you would like on travel days. It takes at least half a day to relocate what with packing, getting to the train station, taking the train, finding your next hotel, orienting to a new place, etc. Florence to Rome may only be 90 minutes on the train, but it is more like 4 hours when you factor in the logistics.

Florence - 4 nights/3 full days

Rome - 4 or 5 nights (3 or 4 full days)

Sorrento - 3 or 4 nights (2 or 3 full days)

That leaves 3 or 4 nights for Calabria...but you need to get back to Naples or Rome to fly out, so allow time for that. You will need to be in the city of departure the night before the flight.

I thought we might be trying to do too much, so I will need to eliminate a city or region on our first trip. Of course that will just insure that we make a 2d and 3d trip over.
Thank you very much for your helpful advice.

Hi Jack

I like Laurel's proposal, but maybe do it in reverse. Start your trip with the family gathering and then work your way north. That way at the end of the trip you are somewhere much more accessible to airports to make departure easier.

Spend your first jet lagged day visiting with family, rather than trying to do a 'productive tourist' something

Fly into Naples and train to Bovalino, meet family, have glass of wine, collapse. Next day start wonderful Italian trip in a less structured way.

With 18 months to plan and 6 adults involved, I am sure there will be several versions before the final one emerges.

Laurel has given you a good plan. But rather than a 7+ hour train ride from Naples, I'd fly from FCO to Reggio Calabria.
1 1/2 hrs. Then a short 1H24m train to Bovalino. Think there are 2 reasonable flights a day.

Then head to the Amalfi Coast and fly out of Naples.