Unexpected layover in Milan

That's a real bummer. I would have a bigger problem getting into Naples that late, then to your hotel in the wee hours. I would verify that you will be able to check-in at that late hour (after Midnight probably) and then arrange for a car service to get you there. Not sure of the hours of Public Transit, but that could be an issue.

As for Milan, maybe plan on stashing bags at the train station in a locker or left luggage, then a walking tour and visiting the Duomo would be enough, maybe some window shopping and a nice long meal.

Is there any way they will put you on an Easyjet flight from MXP-Nap?

I second the Duomo. That's all I had time for on a brief stop, but if you look at TripAdvisor's Things To Do list for Milan, I'm sure you'll find some more options.

I confess that I'd be looking for a day-room at a hotel, though, because I usually don't get even a minute's sleep on overnight flights. (Yes, I know that sleeping in the daytime on Day 1 is supposed to make the jetlag last longer. I don't care.)

Edited to add: Here's the TripAdvisor link.

What is happening about your luggage? Are the airline transferring it from the first flight to the second, or do you have to pick it up and check it in again. If the latter, you have the problem of what to do with it while you are in Milan.

You could book yourself on an Easyjet flight (if one exists), you then would have to pick up your bags and hand them in again at the Easyjet check-in.

Third option, take a train to Napoli. According to http://www.trenitalia.com/tcom-en there are hourly trains, for example:

Departure 10:07 Malpensa Aeroporto T2 Arrival 15:52 Napoli Centrale Price from 72.90 €
Departure 11:07 Malpensa Aeroporto T2 Arrival 17:00 Napoli Centrale Price from 72.90 €
Departure 11:37 Malpensa Aeroporto T2 Arrival 17:13 Napoli Centrale Price from 102.90 €
Departure 12:07 Malpensa Aeroporto T2 Arrival 18:00 Napoli Centrale Price from 72.90 €

That at least would get you to Naples at a civilised time. Those are advanced purchase fares. Pay on the day is €101

If it is 7.50 am, take the train from Milan. Dozens of options that take between four and five hours with no change. Catch a train late morning from Milan and be in Naples, almost downtown by mid afternoon. Why mess with bad connections? And the transfer to Linate is super pain in the butt - back through security, etc. Not worth it.

Be careful if you decide to skip the Linate to Naples flight. Missing one leg of an intinerary can result in the rest of the flights on that itinerary being cancelled. Otherwise looking into alternative options such as Easyjet or trains may be good options.

Call the airline and ask to change the ticket to drop the Linate to Naples leg. They should be able to do that as the schedule change is so great. They might want to re-price your ticket ( higher) but you could argue against that, again on the basis of the drastic difference in schedule ( almost 12 hours later than you want).

Then take the train as suggested if you want a relaxing journey.

I was not suggesting that he skip the Naples leg but since the airlines changed his schedule substantial he has some bargaining room. Just terminate with the airline the incoming flight at Milano. And he can still do whatever the return flight was. And he might save a dollar or two for not flying to Naples. It would be different if his connecting flight was from Malpensa but it is not.

I would get that leg dropped and take the train. Some have no changes of trains, some have one change.

I've had a similar situation getting into Lyon where the airline changed my connection to much, much later. I called a negotiated an in bound early flight to Paris instead and took the train from there. Definitely call the airline back and see what is possible before you resign yourself to a long layover with a less than ideal arrival in Naples.

DJ

Figure out some way to see the Milan Duomo Roof. :)

Thank you for all the suggestions. I spent 4 hours on the phone with the airlines today and it was my birthday. I could not change anything. Since it is a global reservation, if I miss any leg of the trip, the whole thing gets canceled. So I cannot take a train or any other form of transportation to get to Naples earlier. Is it possible to see The Last Supper while in Milan? I have heard that you have to make reservations way in advance. Can we take a tour of Milan from the Malpensa Airport which ends up at the Linate Airport? We will have our luggage with us.

If you can get ticket for the Last Supper, you could go from MXP to LIN, leave your luggage there (https://www.milanairportsguide.com/linate-airport-information.htm), then go to the Last Supper

If you cannot get tickets you could go to the Duomo and the nearby Galleria to pass the time and get a nice lunch, before having to go back to the airport for your flight

I found that I could get this tour with tickets to the last supper. I heard it was really difficult to get tickets so I’m wondering if this is legitimate?

You are booking the following tickets:
https://www.milan-museum.com/
Last Supper & the Best of Milan, date 15-12-2017 at 14,45c (English):
n. 4 full tickets for 272.00 Euro
- Entrance Price 272.00 €
(Entrance Price includes: tickets, temporary exhibition fees, pre-sale fees and online booking service fees)

• Total Price 272.00 €

Total Price is: 272.00 Euro

I’m worried if I Book this in advance and something happens, we will lose the money. Also, I’m traveling with two exhausted college students who may not wish to do this tour when we arrive. What do you think? Can I possibly get tickets or a tour after we arrive in MIlan, or is that crazy?

Jen, I would be hesitant to book any sort of tour for arrival day on an International flight. As you've already (unfortunately) figured out, timing is always ETA and no more than that. Another unexpected delay/complication could cause you to miss the tour and lose the $$. There are other things to see in Milan besides the Last Supper which don't involve a timing commitment.

Editing to add: I don't think I could manage to pay attention to a tour after a long flight. Playing it loose depending on how all of you feel might be a better idea.

You can get tickets for Leonardo's Last Supper ONLY (no tour) from Select Italy, a broker, for under $30 each (based on 2 people), for a total of less than $120 for 4people. I have used them often.

The Last Supper and the Duomo would make a nice stop, plus leave time for a meal.

Select Italy, per their website, has nothing available in December.
14:45 is certainly make-able, just be prepared to lose 272 EUR if your flight is delayed 4 hours or more. Take the Malpensa Express train to Milano Cadorna station. Assume Alitalia is taking care of luggage transfer.

Tickitaly appears to have a few tickets left for 5:45 (17:45) on the 15th.

http://www.tickitaly.com/tickets/last-supper-tickets.php

I know that different people handle overnight flights differently. I do not sleep at all. I would never pre-book a pay-in-advance activity for arrival day, even if it cost just $20 or $30. For something really important to me (and that's the only time I would consider spending as much as that tour costs), I'd even be cautious about booking in advance for Day 2.

If you're really interested in that painting, paying the marked-up fee just to see it makes more sense to me. Maybe check with the other members of your family to see how many want to see it. The non-participants could hang out at a nearby café. There is no single painting in the world that would be worth so much money to me, but I am not religious.

If you arrive on time and folks are feeling pretty awake, perhaps you can pick up a walking tour on the spot.

Last Supper--- No guarantees, but this is what happened on two different trips.

1) Arrived to claim our reservation. Discovered they had no record of our reservation. Produced copy of the email confirmation and they had space for an entry time 30 minutes earlier than our "reservation"

2) Unable to get tickets online prior to travel. Stopped by and got tickets.

Whether they hold a few spaces for "walkups" or had cancellations is unknown, but there is the chance you could get tickets at the door.

Not sure I would do the 272euro package, given your doubts about how up for it some of your family might be, and possible flight delays

Roof of Duomo if it's not crowded, but the amazing tombstones in the cemetery (Cimitero Monumentale di Milano) are sure to be entertaining but low pressure. And free, I think.

Thank you also much for all your advice! One other quick question as far as baggage is concerned. Can a travel accessory be a roll on under the seat bag? It is 16.5 x 12 x 9” (or 41.9 x 30.4 x 22.8cm). Could I take this in addition to a rolling carry-on that is 9 x 21 x 14” (or 23 x 53 x 35cm)? We are traveling on KLM, Air France and Alitalia. I also believe that anything we carry on the plane has to weigh 26 pounds or less?

I'd check each airline's website for its definition of "personal item". Some may have specific size limits. Others may say it's OK if it fits under the seat in front of you. Best to check yourself, to be sure you have current information.