need help with itinerary in northern Italy

First, count nights instead of days. Is two weeks 14 nights including arrival and departure days?

I would prefer to soend 2 nights in Milano or 4 if you want to daytrip to Begamo and Cremona, 2 nights on Lake Como with ferry rides to villages along the lakeshore, Parma is near Bologna if you want to base there for a couple of nights. Venice for 2 days or 4 days with daytrips to Padova and Verona, or a little longer. You need to spend your last night in Milano if you have a morning flight. Trains to the airport from the city start very early, you don't really need a hotel near the airport.

You mention 1-2 nights in each place, personally I prefer fewer bases with more daytrips. So 4 nights Milano, 2 Lake Como, 2 Bologna and 2 Verona or add the Verona nights to Venice, 4 Venice if you daytrip to Verona. That's 12 or 14. One of the Milano nights would be the night before you leave.

As for hotels:

Milano, hotel Garda or Berna near the station; Bologna, Hotel Metropolitan; Venice, Locanda San Marcuolo. Como, depends on which town you choose; Verona, I have no recommendations.

Note that you could fly into Milano and immediately take the train to Venice, then work backwards to Milano so you don't have to spend the night there at the end of your trip just to catch your flight.

I would start in Lake Como as its easy to get to from Milan, then head to Verona, Venice, Bologna, then Milan. Try to stay 2-4 nights in each place, 1 nighters dont give you much time to see or enjoy where you are.

Thanks for your recommendations Zoe & Angela. What cities/villages did you visit in Lake Como? Do you have hotel recommendations there? My mom is in her 80's & walks often for exercise but she prefers not to walk on steep areas or
going up too many stairs. I'm wondering if we should stay in Varenna while visiting the lake. Ideas are appreciated, thanks!
I think Verona will have hotels that are less expensive than the ones in Venice, any ideas? My mom already visited Venice in the past so we may skip it. Have you traveled to Switzerland from Lake Como? If so, what cities do you recommend? What Hotels or B&B's?
I need to figure out our itinerary so I can start booking our hotel rooms. In the past I only booked our first couple of nights but perhaps it's better to have everything arranged & that way it will be less stressful.
Do you know if I need to make a reservation for the train from Milan to Verona or Lake Como?

I actually haven't been to Lake Como, I stayed in Stresa on Lake Maggiore (I liked that there was a bus to Stresa from the airport). Lovely place with beautiful islands with palaces and gardens on them. Most people on these boards suggest Varenna. Yes, its a good idea to book rooms ahead because you will have more choices, RS picks tend to be very popular and book up quickly. Train reservations in advance can be cheaper if there are still Super saver tickets available, but if you are unsure its generally easy enough to buy at the station as you go.

Verona is LOVELY, plus the roads are generally flat and easy to walk. I stayed at Hotel Marco Polo, but its a few blocks away from where you really want to be and is in a tiny unmarked lane that was difficult to spot. Breakfast was good though, and the building is an old monestary.

Thanks again Angela! Stresa on Lake Maggiore looks lovely, judging from the photos I saw on-line. Where did you stay in Stresa?
Did you visit Stresa & Verona on the same trip? What other cities did you visit in northern Italy? I'm having a hard time deciding where to go... We will be there for 12 nights.

We stayed at Hotel Milan au Lac. Its a bit spendy, but the other hotels I was interested in were all booked up. It was a fabulous location, and we had a balcony overlooking the lake even though we only paid for a room with no view. Breakfast was superb.

Verona was done on the same trip (excellent train connection with only a change in Milan), followed by Venice, then we headed south to Florence and Rome.

I would stay in fewer cities and do others as day trips. Verona and Bologna are excellent for that strategy, and both are fairly flat. I would look at Hotel Torcolo in Verona and Albergo Centrale in Bologna. In my experience, accommodations are less expensive in Bologna than in Verona. But you should definitely make your hotel reservations in the near future.

If you are looking for a place in Stresa I highly recommend Hotel Saini Meuble. Gianni is the owner and couldn't have been nicer to us and is a nice quiet place. We were taking the combo trip across Lago Maggiore by boat to Locarno and the train back on a day when the Italian trains were striking. He told us the particular train would run and sure enough it did after a wait in Northern Italy. We got back late and hadn't eaten. He called his friends restaurant and told them we were coming and to take care of us and they did.