Visiting order in North Italy cities

I would fly into Venice and out of Milan. You can do the reverse but early morning flights out of Venice are logistically difficult.

Florence is easy by train from there the classic hilltown visit is Siena for good reasons.
Here's a train map of Tuscan towns:
https://www.wanderingitaly.com/maps/images/tuscany-rail-map.png

You will need to hook through Milan to get to Lake Como and then reverse that to get back to Milan. Look into the train Milan to Varenna-Esino to go to everyone's favorite Como city or take the ferry to Bellagio from there.

You might also look at Lake Garda which is between Venice and Milan. The upper town lakes aren't served by train so it takes a little more effort but depending on when you're going in October the lake areas are starting to close down. I believe Lake Garda's season runs a little longer into October than Lake Como.

Most people find counting nights rather than days is the best way to keep track of where you're going to be each night when making hotel reservations and tracking days with transit. Keeping in mind that 3 nights somewhere is only two uninterrupted days with one part day filled with luggage and transit concerns.

Assuming 13 nights:
Venice 3n
Florence 4n (day trip Siena or other Tuscany adventure)
Como 3n
Milan 3n

I think this is a sensible schedule.

But if we're going to talk preference rather than sense then Florence has the most "must see" things for most people and while many people love Milan I find it to be a big, busy city and generally only spend the time there it requires. I personally love Venice but it is another polarizing city that people love or not. So I would probably steal a day from Milan for Venice although most people would add it to Florence - especially with a day trip or tour planned there as well.

Honestly, I would actually schedule only the single night in Milan before the flight but I have the luxury of having been there several times and having seen what I want to see there. It is necessary for you to go and experience these places yourself and decide what you want to see more of in the future. If I listened to people who said not to go to Venice I wouldn't know how much I love it. Maybe you'll love MIlan and come back and tell me I'm wrong and that's fine if you find a place you love.

Hope that helps,
=Tod

Which is your home airport? That would help determine the best flight combination.

The largest airports in Italy are (in this order): Rome Fiumicino (FCO), Milan Malpensa (MXP), Venice Marco Polo (VCE). Since you are concentrating in the north, that would probably rule out the first.

If you don't want to rent a car to visit wineries, the best option is a private tour/driver. More expensive but wineries tend to be located in rural areas that are not well served (or not served at all) but mass transportation (buses).

Todd, your schedule makes sense. Personally I would:

5 nights Venice...love the city, so relaxing without traffic. Great food and so much to see and do.
5 nights Florence....way too much to do there. I could do 7 nights in Florence without seeing everything.
2 nights Como. 3 days is plenty to see the area
1 night Milan. I actually did 4 hours in Milan. Train to Milan, cab out to see "the Last Supper", stop to visit the duomo, then train down to Santa Maria Ligure for 5 nights.

Either way, they are all beautiful cities and with so much diversity and culture. Don't forget, in Siena stop into St. Catherine's to see her head. You can't not look at her.

Hi everyone, thank you for your valuable input. We just changed our leaving city that we will be departing from New York city. And we now have 14 nights/15 days.

There are many wonderful places in an around north Italy - Bellago, Stresa, Bergamo, Verona, Bolzano, Descanzo de Garda, Sirmione, Treviso, Locarno. All available via rail.

You don't see much of Tuscany without a car. All the cool places are hilltop villages. The one exception might be Sienna, but that does not feel like Tuscany at all. It's a unique town center which is really cool but over touristed with poor food options. On the other hand, I have had many great meals in the real Tuscan towns like Montepulcieano (a RS favorite), Cortona, Volterra (of Twilight fame), San Gnimgiano, ... or down to Orvieto.

While I like Milan a lot, it's not really that much to do there. The cathedral and iconic mall are next to each other, and close to a high end shopping area that is cool, and not too far from an old castle. There is also a China town. Milan Malpensa airport is about 45 minutes outside of town, but there are buses and trains to the central Milan train station Milano Centrale.

Venice is definitely worth seeing once. But I have some to hate that place. It's overcrowded with tourists, and the restaurants are way over priced for substandard food. I would stay in nearby Treviso or another place, then do a day trip into Venice.

Thank you for the input provided here. We have pan out (sort of) on travel order. However now we are planning to rent a car for Tuscany region. We came up with two options. Which one is easier to manage the logistic with car rental pick up and return?. TIA
Option 1:

3 nights @ Venice (pick up car last day at Venice)
4 nights @ Tuscany by car from Venice (return car at Tuscany last day at Tuscany)
3 night @ Florence by train from Tuscany
2 nights @ Como by train from Florence
2 nights @ Milan by train from Como (Leave for MXP at 8am after 2nd night)

Option 2:
3 nights @ Venice

3 nights @ Florence by train from Venice (pick up car last day at Florence)
4 nights @ Tuscany by car from Florence (return car last day at Tuscany)
2 nights @ Como by train from Tuscany
2 nights @ Milan by train from Como (Leave for MXP at 8am after 2nd night)

Option 2 is the way to go.

When you say return the car at Tuscany I presume you intend to return the car in Florence, since you plan to take a train to lake Como afterwards.

Tuscany is not a city. It is a region roughly the size of Massachusetts and Rhode Island combined. Rental agencies are primarily in the provincial capitals of Tuscany, including Florence which is Tuscany’s capital city.

Thank you @ Roberto's help. We will take your suggestion.

I am seeking further input on accommodation, scenic drives, a list of towns and villages to see, and the must visit restaurants and wineries in Tuscany region. For lake Como, we are still debating on our base between Bellagio or Varenna (or other lake towns??). My guess is Varenna thinking it is easier to there by train than to Bellagio from Florence or Milan. Thanks you.

This October, or 2025? You'll probably have a difficult finding accommodations in Lake Como if the trip is 2024, so availability may determine if you're staying in Varenna or Bellagio. We prefer Varenna. We like Hotel du Lac, with lake view and balcony .
For Venice, we stay in the Cannaregio area, on the small back canals. Very charming and there are no crowds, yet 10 minute walk to the vaporetto stop on the Grand Canal. We like Hotel Ai Mori d'Oriente.
Have a great trip!

Regarding the choice of option 1 or 2, it doesn't really matter if you do Florence first then Tuscany or viceversa.

I just chose no. 2 because driving from Venice to Tuscany is unbearably boring (over 3 hours on a freeway in a flat plain then under 50 miles of tunnels through the Appenines range), so my first choice would be to take the train to Florence and pick up the rental car in Florence rather than Venice. Obviously you won't need a car at all during your 3 days in Florence, so make sure you don't have the rental while staying in the city of Florence.