Two week Italy suggestions

Fly in to Venice (easier than flying out of)
It’s the perfect place to get over jet lag
Give Venice 3-4 nights

Then decide where next-maybe 3 other locations -3-4 nights each

Summer will be hot and crowded -especially in Florence and Rome
Consider staying north, Veneto region, visit the Lake region, Dolomites, etc
If you happen to be there during Verona opera season you could attend opera in an ancient arena

You could then fly home from Milan
Book flights as “multi-city” not 2 one way tickets

Do you have to go in the Summer???
Oh, well, perhaps you do.
We love Venice, and staying at the Hotel Ai Mori D'Oriente in the Cannaregio neighborhood is our favorite. There are no crowds here, just charming canals, shops,restaurants. You can actually take a sunset pix without anyone in your frame. Yet, you are a 15 minute walk from the train station, and under ten minute walk to a vaporetto stop on the Grand Canal. And- Row Venice starts in this area, which is a 90 min rowing lesson on the back canals , probably around 100 euros total for the three of you! I like this much more than a 30 minute gondola ride.
I agree, start in Venice, four nights is great, work out your jet lag, and enjoy!
The Dolomites are a great summer option.
And maybe go to Tuscany, to avoid the hot crowded southern cities, and stay in an agriturismo with a pool?
Happy planning!

Yes unfortunately we do have to go in summer. It’s the only time that works for all of us without asking our special needs son’s caregivers to be with him over Christmas/hannukah. Last year we were able to do Rome and Athens in the winter and I agree it was a wonderful time to go!

So fly into Venice! Then, my thoughts are either:
-Dolomites for hiking, lake como and/or cinque terre and then fly out of Milan
Or
-Siena/tuscany, Pompeii/sorrento, fly out of Rome.

Thoughts?

Definitely fly into Venice, 4 nights.
Then train to Florence, 3 nights.
Train to Siena, 2 to 3 nights as base.
Rent a car to visit Tuscany, 2 to 3 nights.
Return rental car, train to Milan, 2 nights.
Fly home from Milan.

I have not rented a car in Tuscany but I’m sure someone here has suggestions for you.

Skip Pompeii this trip. It’s too far south. Plus it will be cooler in the north than in southern Italy in the summer.

Buon Viaggio!

Venice is definitely worth including, especially if it's on your bucket list. For a 2-week trip, you could consider Venice (3 days), Florence/Tuscany (3–4 days), Rome (3–4 days), and then add either the Amalfi Coast or the Lake Como/Dolomites region depending on whether you prefer coastal scenery or mountain adventures. Since you enjoy both outdoor activities and history, the Dolomites offer incredible hiking, while Rome and Florence are packed with museums and ancient sites.

Planning early is a great idea because Italy has so much to offer that it's easy to feel overwhelmed by the options. Speaking of Italian planning tools, I recently came across a useful resource for verifica codice fiscale that may be helpful for anyone dealing with Italian administrative matters.

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My two week trip this July will be Venice>Bologna>Florence>Stresa (Italian Lakes) then fly out of nearby Milan. Since you've already been to Florence, you could substitute the Dolomites/Italian Lakes and keep this trip northern.

Bologna, while being a great town in its own right, offers great day trip options that are cultural (Ravenna mosaics), culinary (Parma), and automotive (Lambo/Ferrari). Maybe that could be your furthest southern destination?

-Dolomites for hiking, lake como and/or cinque terre and then fly out of Milan or Siena/tuscany, Pompeii/sorrento, fly out of Rome.

Pompeii might be a bridge too far this trip, even if flying out of Rome.