Can I wake up in Bologna and still make my Milan early afternoon flight ?

A bit over 2 1/2 hours by fast train with one change (I would not drive) Bologna Centrale to Malpensa T2. Can it be done, yes. Would i be comfortable- maybe not. Assuming 3 hours before departure at airport pretty early departure Bologna. Things do happen.

The only problem is if there is some issue with the rail line on the morning of the 10/17. If there is any kind of delay, you are out of luck getting to Malpensa by 11 am. Safest is to go the evening before and stay at an airport hotel.

A strike will be announced well in advance, so you can plan for that. But unforeseen delays include: accident on the line, electrical power outage, equipment problem, crew problem.

I agree with the above posters.

It boils down to your acceptable level of risk.

Nope, it would stress me out but everyone is different.

Can you? Absolutely. Its physically possible to either drive or take a train (actually trains- a connection would be required) as long as you leave early enough. Like between 06:30 and 07:30. The train is faster than driving, and you dont need to futz around with gas fill ups and drop offs. But as already described, there is a non zero risk that something disrupts the train(s) and leaves insufficient time for a plan B. So should you? How lucky do you feel?

I wouldn’t risk it

Consider staying in Stresa in Lake Maggiore
Closer to Malpensa than Milan, direct airport bus
https://www.safduemila.com/linee/alibus-malpensa-lago-maggiore/

New proposal:
Train to Modena on 10/16
Spend day in Modena and stay overnight
Car service to MXP the next morning. It is about a 2 hour drive.

If you don't mind paying the 300 EUR or so for the car transport.

I wouldn't do it. So many times there are delays on the tracks... this year several times from Milan to Bologna for "unauthorized people" on the tracks... LONG delays.

Not a good idea.

I know I would not sleep well the night before.

I just returned from a trip to Calif. It took an extra hour ( 4 vs 3) to get from Portland to home due to some road construction and a car fire. Weird/random happens.

I knew my house would be there whenever I did get there; you cannot expect your plane to do so.

I will echo what has already been said, only you know your risk tolerance.

To answer your topic question, yes, it can be done. ( but your 'apple cart' can manage only very small bumps )

Happy travels

Revised plan makes sense. If you don’t mind the cost.

Revised plan does not make sense, never mind the cost. You would be at the mercy of heavy car and truck traffic on the A1 autostrada and the heavily traveled Milan ring road (Tangenziale) in commuter hours. You could easily encounter a very long traffic delay without warning.

Why don’t you spend the day in Bologna and then take an evening train to Milan?

This way, you get the full day in Bologna then you can stay overnight in Milan and have an easy trip to Malpensa the next day.

Another vote for getting to Milan the night before.

I’ve been to Italy many many times including six times where I spent three months there each time.
I love Italy, but you have to accept that things don’t always run perfectly.
We love the expression “this is Italy’.

Get to Milan the night before and take Rick‘s advice and go to the wonderful Aperitivo‘s that actually end up as dinner by the canals.

It's simple. You need to find your risk tolerance.

Price a one way ticket from Milan to your final destination. Not months in advance. The same day. (If you do this, don't look at your planned day of travel. Look at prices today.)

I don't know where you are going but I priced a nonstop flight from Milan to New York today. It's $3300 each. Since you used the term "we" I'm guessing there are at least two of you.

So, the question really is, if we miss the flight because we don't want to stay near the airport, are we willing to risk having to pay $6600 to get home.

You see, the airlines don't care if you missed the flight because of transport delays to the airport. They just see more money in the bank.

I fly a lot. My rule is simple....the night before in the same city as my departure airport or no more than one hour to the airport by public transport. I'm also aware of alternatives should my planned transport face issues.

If it's a morning flight, I stay closer to the airport. (I'm not really a morning person.)

It's also italy where I truly believe when babies are taught to speak, the first words out of their mouths are "mama," "dada," and "STRIKE."

If you decide to stay in Milan, then I can recommend the Sheraton at MXP. The location inside the terminal could not be any better. The accommodations and the staff were excellent. It made our travel day stress free.

I have read all of the replies. I am usually risk-averse, but for some reason was willing to take a chance here.

New proposed plan:
Friday morning, last day in Bologna
Friday afternoon train to Milan Central
Travel to Navigli district (have not visited before)
Afternoon/evening and overnight in Navigli district (anyone have an overnight recommendation?)
Saturday morning, car to airport