Help review/change our two week itinerary

You might want to add a day to Venice so you have three nights. Six nights in Florence is more than enough and you'd have time to add time to Venice, and also day trip from Florence to Siena, Lucca and Pisa.

Overall I think it looks great! You could shift the days a little like the previous poster suggested but the flow of destinations looks good. For the last night, you might consider staying at the hotel in the airport (I think it’s still a Sheraton) especially if you have an early flight. You walk out of the lobby directly into the terminal. Good luck with the trip!

I didn't know that about the Sheraton, that is a great tip..Thanks!

Curious from where are you flying into Milan? I'm in Chicago and there is only 1 direct flight, at 10:30pm.
In Milan you have a good itinerary. I'd suggest the hop on/off bus to get a lay of the land. Staying near the train station is convenient. The food is good most places.
I don't know the lake region, but those who do rave about Bellagio.
Venice needs no explanation: just walk and observe.
7 days in Florence is lovely, and you could spend them all in the city. If you and family are renaissance art aficionados. One overlooked museum is the Bargello, mostly sculpture, Donatello, Cellini, ecc
If you appreciate architecture, the Laurentian library (Michaelangelo) is elegant, next to San Lorenzo Church. It isn't always open, you must research. Cappella Medici more ostentatious, but beautiful. Churches overlooked: Santo Spirito (Brunelleschi. In the Oltrarno area across the bridges),
The rest (Uffizi, Accademia, Santa Maria Novella, Santa Croce...) are obvious visits.
You may want to book a tour of Tuscany,. I believe buses can be had to: San Gimignano, Volterra, Chianti villages: Greve, Pantano, Castellina. My favorite area is further south: Siena, Montepulciano, Pienza, San Quirico, Montalcino. The Val D'Orcia Is spectacular! Further south still, but will be out of your way, maybe next time when you include Rome, are Orvieto and Assisi. You could perhaps book tours from Florence? Just suggestions. Buon viaggio

For Lake Como, Varenna is easily accessible from the regional train (1 hr). We are following a similar route this spring. Lodging in the Middle Lakes towns fills up quickly, so secure asap. Como town isn't as charming as Varenna, Bellagio, and Menaggio.
Agree, add a day to Venice, and maybe subtract a night from Florence.
Which Milan airport are you flying into?
Have a great family trip. The itinerary looks fun. Safe travels!

We are flying from KC, have a layover in Philly. Booking through American. I really don't want to, due to the hassle we had with them last year flying to Italy (20+ hr delay in DFW) but it is the cheapest premium economy flight (about 3K less than Delta).

To avoid that split stay in Milan consider going to Como on arrival ( Varenna would be better than Como) you will need to book there asap as lodging is limited

How many NIGHTS do you have on the ground in Italy? Looks like 14.

Varenna 3
train to Venice- needs 3 nights at least
train Florence 5 nights is good-2 day trips

Then put all your Milan nights at end 2 nights is probably enough
As long as your flight is past 10 or 11 in the am you can stay right in Milan night before

For Lake Como, do not stay in the city of Como! The most beautiful area is mid lake; do consider staying at one the following towns: Varenna or Bellagio on east side of lake, and Menaggio, Cadenabia,of Lenno on west side of lake.