How should I propose in Milan?
 

I'm awful at planning something like this and don't know Milan well at all, but I would like to make the moment special. Any ideas?

Any particular reason why you have chosen Milan. A little background on why you will be there, where else you may be goingand what you like would help. Does your intended love opera? Are you foodies? Love shoping? Gardens? Etc.

Milan's not the first place most of us would think of for a dramatic gesture.

Not sure if it's still there, but the coffee shop in the main Rinascente branch used to do a decent enough supper, in a pleasant enough environment (not quite as hohum as "dept store coffee shop" sounds). But with an unbelivable view of the Duomo roof and its gargoyles. THE place for her to assume it's going to be an ordinary evening till she sees the view.

That apart: get the train to Venice. There used to be a Rome-Moscow train which did the Milan-Venice bit almost overnight. From personal experience, I'd say it can be the most romantic place in Italy (still together 35 years later). But just an ordinary fast train, with a day meandering round, works too.

Or do a day trip to Lake Como and propose on a ferry in the middle of the lake or lakeside in the pretty village of Bellagio.

If you insist on Milan (a smoggy, traffic-clogged modern city), I believe you can climb to the roof of the Duomo. That would be pretty special.

Do it in private....

<a smoggy, traffic-clogged modern city>

Wow, a half dozen visits to Milan and I managed to miss the smog and clog. Just lucky I guess.

My husband and I quite like Milan and find it a nice place to spend a few days when in Italy.

Depending on the season, I agree with the suggestion of a day trip to Como. Post for recommendations for a nice restaurant with a view and propose there.

Otherwise, Milan has some great restaurants - are you looking at something more dramatic? Which hotel are you staying in? Enlist the help of the concierge and tell him what you are looking for.