Would appreciate suggestions planning trip to Italy

Erica and Jeff,

Milan usually has pretty good connections. I might think about flying in/out Milan and doing a great circle through those areas.

Verona and Padua are easily linked via train. You could find an nice base in the lakes regions (Lake Garda?) then take the train back and forth. I would also suggest a morning or afternoon in Vicenza to see the Teatro Olimpico.

Fly into Venice and use it as a base to see Verona and Padova - 4 to 5 nights

Train to Ravenna - 2 nights

Train to Bolzano - 3 or 4 nights in the Dolomites (I recommend Ortisei or one of the other Val Gardena towns). You do not need a car. There is an excellent bus into the Val G from Bolzano and once there your lodging will give you a pass to use on the buses in the valley so you can get to the lifts.

Train from Bolzano to Lago di Como via Milano - 3 nights

Back to Milano and fly out - 2 nights

That is 15-16 nights. You say you "need to have a car for Tuscany and in the Dolomites" but you are not going to Tuscany as far as I can see. You really do not need to go to the expense for the Dolomites if go to the Val Gardena, but you might need it for other locations in the mountains.

BTW: what time of year?

Here's my idea for you. First, fly to Venice and stay as long as you choose, then travel around, and fly out of Milano.

Here is your itinerary:
Cortina d'Ampezzo (Heart of the Dolomite's and close to the national park)
Padua
Verona (great food and a very beautiful river)
Sirmione (on the south end of Lake Garda on a peninsula with a great castle)
Ravenna (this would be the stop to drop if you were going to dump one, the mosaics are spectacular but only a few sites)
Belagio (Heart of Lake Como, ferry to other places, if not here then Varenna)
Milan (while here see The Last Supper and Da Vinci museum)

I would do this by rental car. Rent a car in Venice and take off from there. All stops are easily accomplished by car and the total trip is about 750 miles, give or take. Trains eat up your precious time, rental cars are at your total disposal.

If you want to jog down into Tuscany you could do so but you might have to backtrack some to hit your list, check it out on a map. Looks like you have seen a good deal of Tuscany. Maybe go east a little like Assisi, Arrezo, Perugia, Spoleto, Cortona, etc (a lot of Umbria here.) This does take you out of the way. You have 16 days (14 nights) and you may not want to compromise your priority list by heading into Tuscany and Umbria. At any rate, it sounds like a wonderful trip.

Arrive Venice
Padua - 2 nights
Ravenna - 1 night
Verona - 2 nights
(Pick up hire car)
The Dolomites - 3 nights
Tuscany - 4 nights
(Drop off hire car)
Lake Como - 3 nights
Milan - 1 night
Depart Milan

Fly into Florence, out of Milan.

Florence pick up car at the airport head to Tuscany. Start where you are familiar.

Tuscany 4N-Ravenna 1N-Padua (drop car) 2N-Verona 2N-Dolomites 3N-Como 3N-Milan 1N

Florence would be a great starting point, but it's not an option if you are looking at an intercontinental arrival flight.

Thank you all SO much for your recommendations! I think we have it just about figured out now - I will post again when we have finalized our plans 😀 Erica (and Jeff)!