Curious about Milan and Venice

Milan is not at all expensive compared to the towns where most tourists go in Italy. It is known as a base for the fashion industry but you won't notice that if you are not looking to go shopping.

I have been to Venice twice, once in May once in February and no flood.
The most common month this occurs is November:
https://www.venicetoursitaly.it/blog/what-month-does-venice-flood/

Taking into account all the other places you want to visit, you could sure skip Milan this time. If you do include it, the Brera art gallery is great, the roof of the cathedral is fantastic, and the monumental cemetery is our favorite in the world and is free to explore. No need to do any shopping whatsoever. We have only found one restaurant of the type we like, but I'm sure there are more --- we have spent a week total in Milan but just one night at a time when we were coming or going from the airport. Milan is such a transportation hub that, if/when you return to Italy after your first trip, you can easily visit it.

We would love, love, love to be in Venice during a flood, but in all the times we've been there (usually in winter) it's never happened. The city is obviously used to flooding and has quite a system of websites, warnings, doorway water barriers, clean-up crews, and temporary elevated sidewalks in place to deal with it quickly and matter-of-factly. I bet that many of the flood photos that are alarming you are old photos from before the barrier in the lagoon was created or they are of the few unusually high floods. There are maps showing which parts of the city are lower than others and you can be careful not to stay there and not to be on the ground floor. Also, there are disposable plastic boots for sale.

This will depend upon your interests. Milano is one of my least favorite places to visit in Italy. It's too busy/crazy for me. Even Rome or Naples have a more relaxed "feel" to me. But, if you have the right interests, it is certainly a place worth exploring once or twice, presuming that you have already spent time in Rome and Sicily and Umbria and Tuscany and....... The thing with Italy is that there are a seemingly unlimited number of places to visit and being able to prioritize them into an order that suits your own personal preferences takes a bit of planning.
Venice. I held off on Venice for quite a long time, and I wish I hadn't. It is/was special. It is a bit of a challenge to avoid the throngs, but it can be done. The experience of a destination without cars and motorcycles, trains and plane's without wandering into the mountains with a backpack is quite special. I worry about the shift of property ownership that has taken place, owners converting traditional homes and apartments into rentals, but to the casual observer and first-time visitor, it may not be very obvious. It turns out that of the many places we have been in Italy, Venice is my wife's favorite.

We visited both Milano and Venice this past May, and recommend both cities. We loved the tour of the Milano duomo and the rooftop. Enjoyed walking around the Brera district.

We love love Venice! One of our favorite stops. Spent 4 nights in Venice. Stayed at hotel Agli Alboretto in the Dorsoduro district. Much quieter than San Marco. The canals and bridges are amazing. So much to see and do. Just wandering and getting lost is fun!

Milan is a big, busy city. It has it's charms but most of the city is full of busy people doing their things and not concerned with tourists or tourism. This cuts both ways as it is "real" Italy versus a place bent towards tourists but also means you're one of the throng. If you love fashion don't miss the Armani Silos which is a custom museum to Armani built into an old factory where you can actually walk around the clothes and look at them up close not from behind a velvet rope.

Venice is the exact opposite existing mostly for tourism because it is not only not everyday, "real life" Italy it's like something unlike anything else on the planet. Venice is logistically difficult, and can be crowded, confusing and touristy and think everyone should go see it at least once in their lives. The flooding is not that big a deal even when it happens. The city deals with it like other places deal with snow and there are walkways deployed when needed and everyone in the city knows their height number and how high the water will be if "aqua alta" is happening. This is mostly a late winter phenomena combining winds, tides and rainfall but is pretty predictable.

Personally I've been through Milan a number of times because of the airports there and I don't feel any need to go back. But I have been to Venice at least four times and I will always go to Venice given the chance. Your mileage may vary.

Have a great trip,
=Tod

After multiple trips to northern Italy, I'd honestly suggest Bologna over Milan for someone with your interests and budget! Milan certainly has incredible highlights like The Last Supper and the Duomo, but it does lean more cosmopolitan and pricey. Bologna captured our hearts with its terracotta-colored porticoes, incredible food scene, and authentic Italian atmosphere, all at a much gentler price point than Milan.

We were in Venice this last May, 2025, and there was no flooding. I believe the flooding is a seasonal event, around fall-winter, and only certain parts are affected.
We had a wonderful time, and stay in the Cannaregio area, which is on the charming back canals, with no crowds. This is our fourth visit to this part of Venice, and shall return. I always say that if you didn't like Venice, you stayed in the wrong neighborhood.
Milan doesn't really speak to me, except for the Domo.
Hope your trip goes well.

I think probably everyone should visit Venice. I have done so, and consequently have no need to return. Along with Barcelona: two of my least favorite cities. But both obviously popular with a great many people.

Venice is special, don't miss it. Milan has its special places, but doesn't compare to Venice.

As for Venice: my wife has shown me many videos of the floods that occur in the city, which is making us weary of traveling there. Has anyone experienced this flooding, and is there a certain time of year flooding is more prominent?

How old are the videos? Venice installed the MOSE in 2020 which will be lifted if the water level is expected to be too high, so I wouldn't worry about large scale flooding. I've been there a couple of times in December. In 2019 when we were there, they did bring out the raised platforms to walk on. In St Marks square, it does make for some nice pictures with the reflection in the water.