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!

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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.

Sometimes flying into Milan is cheaper than flying into Venice, but seeing Venice from the air is fun! It's easy to train to Venice from Milan.

Both Lake Como and CT will be very crowded, which is made worse by jammed trains. We love Lake Como, but the influencers are ruining the experience. Options we are discussing are Lake Stressa or Lake Garda.

But if you decided on Lake Como, because it is beautiful, perhaps throw some $$$ at the worst issues:
-Private driver from Milan to Varenna, to avoid the SRO (and sometime dangerous) regional trains (no seat reservation possible.) I know I'll be questioned by my use of "dangerous" so this is what I directly observed: train door opens and there's absolutely no room for anyone to get on, so young folks just jump into the crowd. One young man tried to throw his bike into folks- thankfully a rare staff stopped him. Folks running across the tracks in Varenna to board a delayed train before others can. Folks rushing off trains and knocking elderly passengers over.
The regional trains between Milan and Varenna are frequently delayed and /or canceled.

• Stay in a view hotel with a balcony. No matter the crowds below, one can sit on the balcony with a glass of vine and just be.

-Book a private boat to travel around the Middle Lakes area. Or, if using the ferries, buy tickets at 7:30am, get on a ferry around 9:00am, explore around the lakes, and return to home base by about 1:30pm. The lines in Varenna for the ferries and ferry tickets are horrendous by 10:30am.

Sorry this is so long. We love Lake Como. We may return if we decide on the $$$ options.
I'll look for my 2025 Trip Report; perhaps you will find some helpful info.

PS-
The heat and crowds on the Amalfi Coast are even worse, coupled with the very poor transportation infrastructure. The influencers never report on the realities on the ground.

But We do love Italy and wish you a wonderful trip!

https://community.ricksteves.com/travel-forum/trip-reports/italy-in-may-with-the-best-laid-plans-or-why-we-almost-came-home-after-three-days

Please skip over the family issues.

Back in 2017, we flew into Venice, spent three nights in the Dorsoduro neighborhood, which was fantastically convenient for nearly everything we wanted to see and do. And quiet and largely less touristy.

From there, we took a train down to Padua, did laundry, saw St. Anthony’s and the Scrovegni Chapel, plus a bit of the museum on the same site as the Scrovegni. Then trained up to Turin. This was a long day, and I wouldn’t necessarily recommend the same structure, instead might’ve trained back to Venice, stayed another night before departing to Turin.

We stayed 2 nights in Turin, seeing the Sabauda gallery, and bumming about because we were tired. (Hence why I would do the Padua day a bit differently).

From Turin, we got a rental car and drove up to an agriturismo north of Alba. Where we stayed for 7 nights, and went wine tasting all over the Langhe and Roero areas. Beautiful hill towns, amazing wines, neat towns and cities (Asti and Alba), interesting stuff. No Americans to speak of. We ate in Michelin starred restaurants, one my complete accident, went to Bra, the founding city of Slow Food and ate pasta that my wife claimed was beyond the deliciousness that pasta had a right to be.

From there, drove to Cogne, which was super charming. We went up Monte Bianco, had nice dinners, stayed at the most charming B&B ever (Chez Odette), drove with the most insane Italian drivers on twisty mountain roads.

From there, we drove to Milan, turned in the rental car, had a nice lunch, decided against going on the roof of the Duomo (which we had done in 2007), and F’ed off to the airport.

I’m in the early stages of planning our 2027 return, but trip planning is all about making a list of what you want to see and do, and then working backwards to figure out how that’s done.

This forum is good for ideas, but it’s brilliant for the second part, figuring out how to do the things you wanna do.

Max, great ideas for future trips, thanks for sharing your itinerary.

These are all very helpful! Especially the idea of flying out of an airport that isn’t my nearest one. I’m located in Phoenix, so we usually fly out of PHX, but per Pat’s reply I played around with flying out of LAX (a 6 hr drive from us), and it might save a bunch!
Pat HOW did you manage Business class for only $2500/ticket?! I’d love advice!

We are spending 2 weeks in Italy this summer. We are flying in to Venice and out of Naples, working our way south from Venice:

Venice--2 nights

Florence--1 Night (Early Morning train Venice to Florence)

Tuscan Countryside--3 nights (Rent a car)

Rome--3 nights (Drive Tuscany to Rome, drop car on arrival in Rome)

Sorrento--3 nights (Early morning train Rome to Naples)

Amy, LAX business class fares have been very high for late 2025 and 2026. I guess the World Cup and upcoming Olympics are increasing the demand for LAX. We bit the bullet and paid $3900 for our April 2026 business class flights from San Diego to AMS. I tracked the price for nine months, and it never went lower. We used the AARP discount (now discontinued?) with the 10% British Airways Visa discount.
We all need all the help we can get now with airline prices.
Good luck!

We had.a four night stay in Venice a few weeks ago. Crowds were intense; heat and humidity were high, but it was still enjoyable. Corte Campana is a terrific B&B; very reasonably priced with awesome hosts! I would suggest you take the vaporetto to Burano for at least part of a day. El Refolo has yummy cicchetti and a cool local vibe.
After the craziness of Venice, we took the train to the Dolomites and had a magical stay in Ortisei. Fewer crowds, cooler temperatures, gorgeous scenery and crisp mountain air. If you enjoy outdoor activities, the lifts up the mountains are terrific. I wish we had stayed there longer. We did not have a car. Many hotels provide a complimentary public transportation pass.