Milan, lake como, cinque Terre ,florence Venice

Lake Como needs at least one more night.

Welcome!

5 locations in just 8 nights is a lot of moving around and little time being there
Each location changes eats up at least half a day
2 night stay is only 1 full day in each location and you have day trips planned as well
I’d drop 1 or 2 locations and slow down

Both Venice and Florence should have 3 nights

First, reverse the order- early flights out of Venice are a pain, as it's difficult to get to the Venice airport in the early hours.
Note that two nights equals one day. You really have too many destinations, so either add days, if possible, or cut out a stop. I wouldn't spend any nights in Milan, (unless you have a late-arriving flight). Go straight to Varenna, Lake Como, and sleep there. The mornings and nights are absolutely beautiful around the Lake. Or eliminate Lake Como and go to the CT.
The CT will be packed and very hot in August- just be prepared.
Florence will also be very hot and humid, but visiting air conditioned wineries would really help out. Tours by Roberto come highly recommended in the RS videos and guide books.
All your hotels must have air conditioning in the summer months- double check.
Have a great family trip and enjoy. Safe travels!

If we start in Venice for three nights and do Florence for three nights maybe we can do a day trip to ct ? Then lake como 2 night fly out from Milan back to nNY

maybe we can do a day trip to ct ?

A day trip to the CT from Florence in August means that you'll be arriving in CT with the hordes of other daytrippers. A day in Siena might be much more enjoyable. Venice and Como should be enough time on the water,

Have you booked flights yet?

While it is easier to fly in to Venice rather than out of- if it is a direct to US flight (to EWR) those flights tend to leave later morning 11-12 ish so it’s doable.

If you end at Lake Como you will have to get to Milan or near MXP the night before departure
It’s too far/risky to travel in the am for a flight so that is sort of a wasted night

Fly to Milan
To Lake Como 2 nights
Train to Florence 3 nights with 1 day trip
Train to Venice 3 nights with visit to lagoon islands
Fly home

CT will be slammed with visitors
Actually everywhere will be crowded but I would day trip to Siena or Lucca/Pisa instead
You have water and views in Venice and Como

What is your son interested in?
If you aren’t museum and art lovers maybe look at Bologna rather than Florence

8 days?
5 Milano
3 Varenna
Slow down! Enjoy life.

I agree with the others that your proposed Itinerary is too rushed, and will be exhausting in August. Since the end of the pandemic Italy has been dreadfully crowded, and there's no indication that this year will be any different. I'd suggest a more relaxed Itinerary which will allow you to enjoy the places you're seeing more, and that will probably mean eliminating at least one destination from your proposed Itinerary (IMO, Venice is the outlier).

A few thoughts......

• It's likely that Venice will be extremely hot and crowded in August, and it's probably not going to be like you remember it.
• When you arrive in Milan, you might consider heading straight for Lake Como, and the town of Varenna is a big favourite with many here. It's about an hour from Milan by train. I can't think of a better place to recover from jet lag!
• If you'd really like to see the Cinque Terre, go there after Varenna. There's a direct train from Milano Centrale to Monterosso in the early afternoon as I recall (travel time about 3H). The biggest problem might be getting a hotel booking in the C.T. If you decide on that option, you'll have to start booking soon!. Check the Rick Steves Italy guidebook for accommodation suggestions. The C.T. and area trains will likely be VERY crowded in the day time (especially if there are cruise ships in the vicinity), but the evenings are generally not too bad. One nice activity is to take the ferry to get a view of the five towns from the ocean.
• From the C.T. you could travel to Florence for a few days, with day trips to a winery or perhaps to Siena (by bus).
• Florence has a small airport for your return flight, although travel from there would probably mean a stop at a larger hub airport like Frankfurt..... OR you could travel to Rome Fiumicino via fast train (about 2H:20M) for your flight home.

I don't know if the Euro zone ETIAS system will be up & running by then, but you'll have to check that - https://travel-europe.europa.eu/etias_en .

There are all kinds of possibilities. Good luck with your planning!

Thinking CT needs to be done another time after reading posts
Although August is a busy time to travel it’s our only option
We did 5 nights in Sorrento last summer in August so I know it’s crowded that time of year .

Venice lake como and Florence seemed doable
Flying in on a sat
Sat - arrive in Venice 2 night stay
Sun - Venice
Monday - leave for florence ( 3 nights)
Tuesday - sienna
Wednesday - explore florence
Thursday - train to lake como (3 nights)
Friday - lake como
Sat - lake como
Sunday - fly back ewr

Or reverse ?

Gee1209,
This last revision seems very doable. Again, check on flight times out of Venice. If your times aren't early morning, then you could run the itinerary either way.
Also, check lodging availability, especially in Varenna, Lake Como. That may determine which way you follow the proposed itinerary. Do secure lodging asap.
You probably need to be in Milan the night before your flight home.
It's always fun watching plans evolve after research and consideration. Have a wonderful trip!

More time in Florence and Venice. Don't spend the night in CT, just do it on the way.