Four City trip to Northern Italy - how long in each city?

My initial thought is 4 nights Venice (3 full days), 4-5 nights Florence (3-4 full days with day trips), 3 nights Cinque Terre (2 full days) and 3-4 nights Lake Como (2-3 full days). Depending on when your flight departs from Milan, you may or may not need to stay either in Milan or near the airport the last night. That matches your 14-16 days target.

Are you aware that a private water taxi will probably be very expensive? You might give the location of your Airbnb and see whether someone here has an idea of what it will cost.

Count nights on the ground, not days.
Remember that 2 nights in a place is only 1 full day in a place. 3 nights in a place is 2 full days, and so on.

VENICE (& THE LAGOON ISLANDS):
3 nights

FLORENCE:
3 nights
(if you want to take day trips from Florence to other Tuscan towns, add one night for any day trip you plan to take

CINQUE TERRE:
2 Nights

LAKE COMO:
3 Nights

MILAN
1 night (before flight home)

I used 12 nights, which I think is the minimum I would spend at those locations.
If you have more to spare, allocate according to your preference.

For a first trip, this would give you a great start.
Think in terms of nights on the ground as opposed to days.

4 nights Venice. Some good helpful info at...
https://quickvenice.com

2-3 nights for Florence itself, then add 1 day for each possible day trip such as Siena, Bologna, a wine tour or Tuscan village tour.

3-4 nights Cinque Terre, or a little further to Santa Margherita Liguria area of the Italian Riveria. https://www.neverendingvoyage.com/italian-riviera-things-to-do/

3 nights Lake Como. Look at Varenna or Bellagio.

Then, unless you have a late flight out of MXP,
1 night Milan.

Venice: 4 nights if you take an out of town excursion one of the full days, otherwise 3 nights. Florence: Same. Cinque T: 3 nights. Are you all big hikers? Consider a day trip to - or even sleep in Santa Margharita/Portifino - easy by train from Monterosso al Mare. Real nice up there. After all that, take the direct train to Milano Centrale (3 hrs) and then up to Varenna (1 hour). Sleep in Varenna or Belagio 3 nights, maybe 4. You may also look at inserting Lucca in between Florence and the CT for two nights. This is my quick take after visiting these towns in Sept 2019. Have fun.

Thank you all for the replies! Even though this trip is almost a year away, we talk about it almost every day and are looking forward to it so much. The iteneraries suggested make a lot of sense, and are right in line with what we’ve been thinking. It takes a bit of traveling to realize “nights on the ground” don’t equal “days to explore” so we’ve started padding the nights when we can afford to do this.

@acraven I will check on the costs of the Water Taxi…good point! My Swedish cousin told us that the “only way” to arrive in Venice is by water via Marco Polo airport! LOL A splurge maybe, but he is very good at giving things a sense of occasion, so we are likely to take him at his word here!

Spending the last night in Milan makes much more sense too, depending on our departure time.

Thanks again everyone for sharing your knowledge of traveling in Italy!

Betty

I have not visited the Lake district of Italy, but it has very distinct seasons. Some of the most famous gardens or attractions may have closed, even if it's less crowded in October.

Private water taxi is a matter of budget, luggage handling and convenience. Arriving by train and walking to the Vaporetto stop is not a disappointment or letdown. How many stairs would you have to negotiate with or without the water taxi? That question can be hard to answer in Venice.

How many stairs would you have to negotiate

Try https://europeforvisitors.com/venice/bridges/

l.p.enersen - Thank you for this great reference tool - this will help a lot when choosing our Air B&B!

The Alilaguna water bus will get you into the Venice city center by water and it’s reasonably priced. One stop is right by the Rialto Bridge. I advise taking the expensive taxi ride to Milan airport (around 100 Euros), I did a one-night stay at the airport and it was a false economy in terms of convenience. The train is another way to go depending upon your flight time, but I did not want to risk it having to catch a 6 a.m. train on the day of departure.

I would stay four nights each in Venice and Florence. Maybe three in Varenna and two in CT. You have the order right, and good call starting with Venice. I hope you are lucky with the weather!

There is much in northern Italy that is very worthy you are not visiting: Bolzano, Verona, Ravenna for starters. (I was in each of these places this past May). Many of these are advanced topics, appropriate for me as six-time vistor--but they are really great. It's your trip, and you should visit the places you want. It's understandable to want to do the greatest hits, and good for you for somewhat limiting the geographical coverage.

I have included Italy on six of my nineteen Europe trips, and three of those were entirely within Italy. For me Rome is the greatest place in Italy. I am not even a city person, I have always lived in the suburbs. But this city is great. See it on a future trip if you can.

Italy is at once exasperating and delightful. Be prepared for that. Add a night or two if you can, you will not regret it.

That is such a hard question. The more time you have in each place, the more you'll be able to explore and enjoy.

Venice. If you are ready to splurge, a taxi is not at all a bad idea. The trip across the lagoon can be lovely, but if you're on the standard Alilaguna boat, it's not very comfortable and the seating doesn't offer much of a view. 3 nights minimum since you are likely to be jetlagged. Give yourselves a little time to relax and wander.

My copy of The Agony and the Ecstasy has a list of all of Michelangelo's extant works, many of which are in Florence. If you want to see them, you'll need a couple days to do it, but you'll have time to see a lot of other beautiful works of art in the same places. In my limited experience, Florence is much more crowded on the weekends, so if you can, arrange to be there Mon-Fri. I don't think it matters in Venice. Crowding in the CT is probably more a factor of cruise ship schedules than anything else. I think I would figure out how many nights to spend in each of your other stops, then allot the rest to Florence. There's so much to see and there are worthy day trips too.

I haven't been to Lake Como yet. Since you are flying out of MIlan, consider spending 2 nights there and using a full day to take in its sights. The Duomo is well worth the time, and wandering among the rooftop spires is interesting and you'll have good views too. You can tour La Scala and visit the museum. I enjoyed the Sforza Castle and its museums.

Depending on how much art/architecture you want to enjoy . . . stop in Padua on the way to Florence (luggage storage at the train station) and see the Giotto frescoes. Stop in Pisa on the way to the CT (luggage storage here too) and visit the Campo dei Miracoli - see and maybe climb the Leaning Tower, the church and grounds are beautiful and the baptistry is exceptional.

Again, I can’t thank you all enough for the information and suggestions. I am feeling more confident about the amount of time to spend in each city now, and will be able to seriously start the planning!

I stayed at the MOXY the last time I was departing from Malpensa (Milan airport). It’s an extremely handy modern hotel, and you just take the train out to the airport the night before, and stay there across from one of the airport terminals.

For the Lakes
The first half of October can be beautiful weather, and at least on Lago Maggiore, the summer ferry season and sites go through the second weekend in October. Later in October ferry options might be more limited and great chance of rain and cooler weather.

Before booking flights for your final itinerary, be sure to check ferry and site schedules and entry days times so you are not disappointed.