advice needed - Italian trip..

I always prefer to stay at my departing city the night before my flight home.

You can stay at a hotel near the train station so you can easily catch the Malpensa Express to the airport.

Although in theory you have plenty of time to get to Malpensa, strange things sometimes do happen (strike, equipment malfunction, suicide by train, etc.), and the penalty for missing that flight would be painful. Your airline would have no responsibility, and you'd almost certainly have to buy three one-way tickets home at last-minute prices. I would return to Milan the day before the flight (late in the day) and plan some nice sightseeing for the last day.

If you decide to roll the dice on this, I highly recommend that you not take the latest train that is scheduled to get you to the airport on time. That would be cutting it way too close.

I am feeling dense, but the cost of hotel in Milan would not likely to be higher than in Rome, so how is plan B an 'additional' cost?

As already mentioned, if doing to Rome to Milan on the day of your flight , I would leave much earlier than the 'just in time' schedule you propose.

Did you really save that much on airfare to cover the train cost to/from Milan and factor in some value for your time?

Plan B is to stay in Milan for the night (additional costs), after
returning from Rome and then take the next night's flight..

Do you mean that you haven't booked your plane yet? Plan B means adding 1 night to your current itinerary (posted below) so you can be in Milan the night before a flight which leaves at 10:25 pm daily?

Day 1 - Reach Milan (Malpensa?) at night; "hope to arrive in Milan at around 7:30 pm"; sleep Milan
Day 2 - Milan
Day 3 - Train from Milan to Florence
Day 4 - Florence
Day 5 - Florence
Day 6- Train from Florence to Rome
Day 7 - Rome
Day 8 PLAN A: - afternoon train from Rome to Milan with onward flight to Doha at 10:25 pm
Day 8 PLAN B: late afternoon train from Rome to Milan, stay in Milan, fly home Day 9

So you may not have booked your flights and hotels yet? If that's the case, your itinerary as it stands is a lot of travel time for little sightseeing time in Rome. If you can swing an additional night, as you are considering, and as I'd strongly recommend, you might consider this instead?

Day 1 - Arrive in Milan 7:30 PM; sleep Milan
Day 2 - Train from Milan to Florence
Day 3 - Florence
Day 4 - Florence
Day 5 - Train from Florence to Rome
Day 6- Rome
Day 7 - Rome
Day 8 - afternoon train from Rome to Milan
Day 9 - fly home 10:25 pm

While I know your (tentative) arrival in Milan is in the evening, you still should have time to get through immigration, into the city and to bed in time for a good night's sleep, how you all manage jet lag excepting. Putting your sightseeing time in Milan at the end of the trip would place you nearer to where you want to be for your flight and give you more than 1 full day in Rome, which I think you need and would be well worth the cost of an extra night. You will also have a much more relaxed departure day.

Editing to add: on day 9, I'm quite sure your hotel will store your bags for you after checkout. Do your sightseeing and collect them before heading off to Malpensa, assuming that's your departure airport.

The last three times we stayed in an apartment or hotel 10 minutes walk to the train station in Milan, I timed it as 4 hours door to gate. I don't remember exactly why it took so long except that Malpensa is a big airport and I remember having to criss-cross it because checkin was way to the left from the entrance and the gate was way to the right. Planes board very early these days, too. So, what looks possible on paper may not work out well in real life, even without transportation strikes or missed connections. Give yourselves more time. Arrive in Milan and stay there the night before. You could still have most of the day in Rome.

Hi. I have not booked my flights yet due to the changing itinerary and we were still thinking of the things that we would definitely like to do and allocate days accordingly for that.

Based on the feedback that I received, I did a cost analysis once again and see that the added cost of accommodation in Milan (2 nights since the flight leaves Milan late night and check out is at 11:00), return train from Milan to Rome, fatigue makes it a costly and tiring return trip from Rome to Milan..

As such, the current itinerary stands as below with additional days -
Day 0 - Reach Milan at 7:25 pm
Day 1 - Milan
Day 2 - PM Train from Milan to Verona
Day 3 - Verona - day trips?
Day 4 - PM Train from Verona to Florence
Day 5- Florence
Day 6 - Florence
Day 7- PM Train from Florence to Rome
Day 8 - Rome
Day 9 - Rome
Day 10 - Rome
Day 11 - Return flight from Rome in evening

I would like to fit in a wine & cheese tour somewhere in between.. How does this look?

Choosing to fly into Milan and out of Rome is an EXCELLENT decision. It's going to save you tedious backtracking time and money to Milan that you can use for something better...

...and which you are doing by adding some days to your trip. I can promise you that you will be glad you did, and especially so traveling with a very young child. Your new itinerary looks good to me although I can't weigh in on Verona as I've not yet been there. I can tell you that when it comes to day trips, Florence is an excellent base for a number of those, and day trips from a base may be preferable to making another city/hotel shift but it's up to you.

I see that you've noted all of your train trips for the "PM"? They're more likely to be in morning/late morning after checkout.

I am assuming that you are traveling east with the very late evening departure. However, I am surprised that an open jaw ticket would be more expensive especially when the cost and inconvenience of returning to Milan is added to the RT ticket. If I followed you plan I probably would leave Rome in the AM, maybe spend half a day in Milan, and then on to the airport. The probability of a rail delay between Rome and Milan is extremely low but not impossible so I would allow more time.

We are planning our third trip to Italy for this fall, and we are planning on going back to Verona. Several years ago we spent one night there, luckily found a charming hotel ( we didn't have any reservations ), and only had about 24 hours there. We loved it ! It is a beautiful place and I don't think you could go wrong by planning some time there . ( can't go wrong planning anything in Italy, actually ) Hope you enjoy your trip. Give yourself more time than what you think you need, as everyone else has suggested.

Yes. the train trips are all to be in late morning after checkout.

Haven't yet decided what to do in Verona.. Skipped Venice as I personally felt it to be an over-rated place with tourists walking shoulder-to-shoulder and I thought i'd rather spend the bucks elsewhere.. i am still open to exploring other places, if Verona does not work out.. any suggestions for a nice place after leaving Milan and before reaching Florence. Florence accommodation is pretty much sold out and I might not be able to move the Florence dates any more..

Your last itinerary is much more manageable. I can see why you want the evening train between Milan and Verona, it gives you additional time to see sites in this large city.

I do however agree with Kathy, on your transfers to Florence and Rome,
Use a mid morning train.

Doing so Verona-Florence will give you a full day to do a tour into the countryside. I think otherwise you will be pressed for time especially with a little one. Highly recommend this company. The Crete Senesi may fit.

http://www.toursbyroberto.com

The same goes for your Florence- Rome transfer. It will allow for a more leisurely time in this great city.

Edit: Not a novice with a 3 year old, did Venice, Florence, Rome with my Grandaughter many years ago.

I am having second thoughts on whether to cancel Verona and add those days to Florence or Siena so that I can stay more time in Florence / Siena and use that as a base. However, Florence is a costly base in June 2018..

If you do drop Verona, I'd be inclined to add that night to Florence. It has so many more options for day trips, both by bus and train.

Have you considered apartments? Usually less expensive, and it would give you the ability to cook some meals.