Milan or Venus

You mean Venice?

Venice over Milan! Absolutely

Venus? The planet?

Now that’s a trip of a life time. 🤓

In response to your question?

Direct flight.

If you are leaving on the 8th, you’ll arrive in Italy on the 9th. You plan to be in Rome on the 10th.

In my opinion I’d go directly to Rome. You’ll only have a partial day on the 9th and both Venice and Milan need more time than that.

It's a long flight to Venus....

Not sure I get your schedule; if you leave NY on the 8th, you will get to Italy either
late the night of the 8th (if you take a day flight), or the morning of the 9th, and you
say you want to be in Rome on the 10th. So at best you have a day to see either
Rome or Venice, and a day & a half to see Rome.

So I say forget Milan or Venice and spend the extra day in Rome.

If you want to try and cram one of the additional cities in, I say Milan, for the simple
reason that you can see a few things in a day, and Venice takes a bit of time to figure
out how to navigate. And having the time to wander around the back streets, other
islands, and get lost is part of the fun.

For all the reasons given above, a third vote here for going directly to Rome. You're likely arriving on the 9th so you'd have one partial, possibly jet-lagged day + 2 full days for Rome. Given the amount of interesting things the city has to offer, you'll need every minute of it! :O)

4 nights/3.5 days is my recommended minimum for Rome.

Another vote for Venus. Venusians are fun and friendly (or so I heard from a friend in Houston who works for NASA). They make a type of spaghetti called “bigoli”, usually served with a sardine and onion sauce. Order it. It’s an expensive place, so bring lots of money, or “schei” in Venusian (pronounce: Skay).

Roberto, your post brings back fond memories of our beloved Venus. Maybe one day we can return, hopefully it hasn’t become overcrowded post covid.

I think you should be among the first humans to tour Venus.

You’ll have to let us know what it’s like. I’m wondering what form art takes (has Venus taken any art that needs to be returned to Earth?), what the architecture looks like (does Venus also enjoy cube homes like in Rotterdam?), what type of food they eat (do they, like many on Earth, reject meatloaf?).

Really, going to be fun to hear about Venus. I hope you share your findings with us, but wonder if the NY Times will get first chance at reporting on it.

Why not just fly directly to Rome?
There are surely direct flights to Rome from NYC

Christine: I'm flying in Business Class using points. So, because I am using points, I had to be a little creative, so Milan or "Venice" were my choices.
THANKS FOR ALL of your responses!!

In either case, you won't have a lot of time in the arrival city. Will you then take a train to Rome? If so, Milan is about 3 hours, while Venice is 4 hours.

I would opt for Venice - it is unlike any other city. You can take the alilaguna boat from the airport directly to Venice proper. (Note: plan to stay in Venice, not Mestre.) Once in Venice, you don't really have to worry about transportation. Arrange to drop your luggage at your hotel, and then go out and explore, and take in the sights and sounds that make this city so special. It is quite small and you can cover lots of territory in 1 or 1.5 days.

Don't forget - you'll be jet lagged, so you may have a to take a bit of a break in the afternoon, but that's ok. Venice is alive late at night. I'd suggest taking a vaporetto after most of the day trippers have gone, or in the morning before they come. Sit in the back where you have open view to the canals - it's glorious.

I have visited Venice for anywhere from 1 - 7 nights (just finishing up a week now), and I think even a day trip to Venice is worth it!

Venice is a great place to get over jet lag, I’d go there

Get a hotel near train station so easy to move on to Rome next day

Venice is great, but if you are really limited on time, I'd save it for when you can spend a few nights. Well worth it. On the other hand you can see the main sights in Milan in a day. We flew in before sunset, checked out the Duomo and Galleria that night (beautiful), climbed to the roof next morning, and zipped over to Last Supper before catching a train to Cinque Terrre mid-afternoon. It required some careful planning and advance reservations, but we didn't feel rushed and saw what we wanted to see.