Flying into and out of Milan - should we skip it anyways?

Skip Milan.
Did you price every combo of multi-city flights? It's not a huge deal to hop on a train from Milan to Venice on arrival, but it would help if you could fly out of Rome at least.
Very carefully compare all of your options, because to me arriving in Venice absolutely screams "honeymoon" (versus having to trod through train stations) and if the difference is in the hundreds and not the thousands, your time and convenience is worth it. Just thoughts to ponder, congrats and good luck!

Thank you for the response!

Indeed, flying directly into Venice would not be much more cost, I think then we will do that. Flying back is where there's the major difference in the cost, so we would still consider flying out of Milan rather than Rome.

I think that will be well worth it. When you depart, you could leave it late in the day and stay at an airport hotel, or arrive late morning and check out Milan, either way I think you'll be happiest if you maximize your time in the "big three" and have that easier (and wow factor) arrival.

Make sure you count the cost of the train ride in your calculation.

Personally, I like the Duomo in Milan a lot and would consider taking a train in the afternoon to be able to see it. I would then stay near the train station and go directly to the airport the next day. I have stayed near the airport and found that it wasn't that much quicker than staying near the train station.

But I don't like Rome as much as some others.

But easiest certainly is flying out of Rome.

I never know how to answer "worth" questions, but here goes anyway!

No, I wouldn't stay in Milan on this short trip. Have done it many times, but on longer trips.

Yes, immediate train to Venice is perfectly doable and we have done it --- 50 minutes from the airport to the central train station and then 2.5 hours from Milano Centrale to Venice, cost $75 total each person.

Rome back to Milan is only 3 hours by fast train, $118 each, so no need for a night train. Airport hotel costs money.

Have you already added up all these costs and flying into and out of Milan is still much less expensive? It is sure more time-consuming and more time spent on trains instead of in cities. We used to fly in and out of Milan to save money and now we don't.

If it were my honeymoon (full disclosure: we went car camping), and knowing nothing about your interests, I would be inclined to fly into Venice, spend 4 or 5 nights, and then pick either Florence or Rome to stay in and to fly home from. It would be interesting to add up the costs involved with just two cities and the time spent on trains and just in things like being able to avoid an airport hotel. One of our sons and his wife honeymooned in Italy and I think they wished the trip had been more relaxing and with fewer trains and buses.

Thank you all for your replies!

I think the point about travel time is a good one. I hadn't necessarily been considering it in (because the nonstop Milan flight is so much shorter than the 2-trip flights) but it's true that it would cut into time actually doing things.

So maybe after all, just skip Milan altogether, flight or otherwise!

Congratulations on your upcoming wedding!

I would suggest these for the number of days in Venice, Florence, and Rome (3,3,4 days). Your first day will be jet lag arrival, so the first city is getting less time, and there’s a lot to enjoy in unique Venice, my favorite Italian city.

And just in case you’re not aware, you are going to the three cities that have tourist crowds. If you’re okay with it, that’s fine. If you want suggestions for other options in Italy, let us know what you’re hoping to do, and we can make recommendations.

Will put another curve in your plans. First, price your ticket into Milan and home from Rome. Unless there is a big promotion pricing for Milan it should be about the same price. Then look at a map. Unfortunately, Rome and Venice are slightly in the opposite directions so you will have a few hours of back tracking. With limited time I would try to minimize train travel. Every time you use the train you will lose a half day of sightseeing if not more. I personally would save Venice for another trip. Although there is a tendency to overlook Milan, I like it. It has great sites and can easily occupied at least a couple of days. I would fly into Milan and then head to Cinque Terre, or Florence, Pisa (?), maybe be Siene, and finally Rome. Cannot do them all but pick a couple that appeal to you. You need to spend sometime with travel videos to get a general feel. Most libraries have a good selection of Steves' travel videos.

PS -- I find the Rome airport much easier to get to and use over the Milan airport. I would prefer to depart from Rome.