Suggestion for additions to itinerary

It's likely to be really hot then, but you know that right?
The sun, heat and humidity will make you need lots of water so plan for that. Also it decreases how much you can do, somewhat.
Don't try to do too much (perhaps assume you'll be back?).
Surprisingly, beaches can be a bit difficult to get to.
Architecture, you're in the right place for that. And for churches.

Yes, I know it will be hot but we are from Kansas so we get hot. It’s the only time we can go because of school activities.

2 nights is not 3 days, it is one FULL day and two partial days. Almost anywhere in the Dolomites will take most of a day to get to, ditto the Amalfi Coast. Cut those out and plan to return. Add more time to your 4 planned stops of Venice, Florence, the Cinque Terre, and Rome. Travel in that order. With 14 nights (assuming you land on June 24) I recommend 3 nights Venice, 4 Florence to allow for a day trip or two, 3 in the Cinque Terre, and 4 in Rome. Take a night away from Florence and add it to Rome if you plan to day trip to Pompeii and GO EARLY.

It will be cooler at altitude up in the Dolomites than at the other places you mention. Don't try to stay in one of the valley cities like Bolzano (but see the Iceman at the museum there) or Bressanone. They are lovely, but they are hot, and many moderately priced lodgings lack air conditioning. Stay up in the mountains in a place like Ortisei.

Exactly how many nights are you planning on spending in Italy? Are you sure you have extra time to play with? I'd want a decent amount of time in Rome, Florence and Venice before I started looking elsewhere unless it was a purely weather-driven decision.

Padua is an interesting city that's a short train ride from Venice, but I confess a personal reluctance to make day-trips from a city like Venice where hotel rates tend to be very high. For you there is the Scrovegni Chapel (tickets cannot be reserved on the day of the visit).

From Rome I'd consider Orvieto. It's a nice, walkable town with colorful architecture and magnificent duomo. You take a funicular up to the historic town from the railroad station.

I think few people will recommend a day-trip from Rome to Pompeii in the summer. It will be a very long trip, and it will be hot. Ostia Antica is much more conveniently located, and there are some trees. However, I can understand the draw of Pompeii when you have school-age children.

It will not only be hot, it will be HUMID as well but just as importantly, it will be crowded in all the places you have mentioned. As in WDW crowded. Which all combines to reduce what you can accomplish in a day. You only have 2 weeks, and your itinerary already includes a lot of city changes, which will cost a half day each day you do it. I don't think you have time to see the high points in all the places you already have planned, let alone add more.

If you don't already have your tickets, I hope you'll look closely at an open jaw ( multicity) ticket where you can fly into Venice then fly home from Rome or Naples. That will save time having to backtrack to your arrival city the night before you come home.

Venice 2N, train to Florence 3N. Bus to Siena 2N, rent a car to Montepulciano area and tour Tuscany 3N. Drop car in Orvieto 1N before a train to Rome 4N.

Name one thing you want to see in Pisa, other than the tower. CT and Pompeii will eat up a lot of travel time and require backtracking. This itinerary would have very short travel days. Hertz has offices in Siena and Orvieto. GPS makes it relatively easy.

As Laurel stated, Venice 3, Florence 4, day trip to Lucca & Pisa combined,or another Tuscan town, Cinque Terre 3, Rome 4 with a day trip to Anzio ( beach & WWII museum). Ostia Antica for ruins similar to Pompeii with more shade.

How does this look to you? Fly into Venice and out of either Rome or Sorrento. If you plan carefully you can hit most of your list. I'd really consider dropping the Cinque Terre (going to be very, very crowded). The main 3 (for most people) are Venice, Florence and Rome. For something different - after Venice head to Bolzano and up to Castelrotto (by white-knuckle bus) for a couple of nights in the Dolomites. It'll take you some time to get to Florence from there. Stay a few nights in Florence and maybe day trip to Siena (the Palio preparations will be in full swing - you don't need to be there on July 1st to enjoy it!). Florence will be crowded, hot and humid but it is an amazing place. Then finish up heading south. From Florence you can Freccia (high speed train) to Rome and onto Naples. I love Sorrento and it gives you easy access to Capri, the Amalfi Coast and Pompeii. If you are flying home from Naples then spend a few nights in Rome first. Or the other way around if your flight is from Rome. My goodness but this looks busy . . . even to me! Family meeting: do you want to be tourists and 'see' Italy or do you want to 'experience' Italy? I like to slow down, enjoy being there and not feel rushed by a check-list.

Somehow I don't think I've made things easier for you. Sorry. Get a map, check train schedules (trenitalial.it, which won't be available on your dates for another month or so but you can get an idea of travel times), prioritize your to do list, watch YouTube videos to wet your appetitie and search hotel sites or appartment rentals! Make the planning part of the fun. It isn't too early. Heck, this will be year 16 for me and I started making plans on the plane coming home last July!

You'll find lots of help and great advice on this site. I get the impression we all love sharing our success stories from our travels! ENJOY!!!!

A day trip to Pompeii from Rome is doable. Know in advance that this will be an ALL DAY expedition. It will be hot. But it is doable. If you're not comfortable driving the distance or taking public transportation, you can look into tours that do the day trip from Rome.

Apparently you have 14 days to visit Rome, Pompeii, Florence, Pisa, Cinque Terre and Venice.

That is a lot to see in two weeks and possible. Having been to Italy several times my favorite city is Rome. There is so much to see there.

Rome- plan on at least 5 nights
Pompeii- a day trip would be too much, so I suggest one night in Sorrento then returning back north
Florence- 4 nights and add another for a day trip to Sienna.
Pisa, Lucca and Cinque Terre would take a couple of days.
That leaves you with 2 nights in Venice, when you need at least 3.

Forget beaches, the beaches in northern Italy are not so good. Lots of History, Art, architecture and great food.

I suggest leaving out Cinque Terre. Do a day trip to Sienna from Florence. You can always come back to Italy and visit Umbria, Ravenna, Capri, Amalfi Coast, Pisa, Lucca, Cinque Terre, Milan, Verona, the Dolomites and more.

Thank you everyone for the great ideas. My family and I like to see the highlights and have planned three previous trips to Europe by staying 1 or 2 nights per town/city except in London, Paris or Rome where we have stayed 3 nights. I know most don’t suggest this, but that’s how we travel. We can relax when we get home because there are too many great things to see. Yes, we can go back but there are so many other countries we haven’t seen yet. I appreciate everyone’s thoughts!