@ Woinparis: :-)
@ colduphere: ((Y))

I hate the small restaurants in the Galleria Vittorio Emanuele as they are overpriced, but I guess that in winter one of them could be the best place in Milan to propose. I can think some other places (for example the gardens at Porta Venezia or Bellagio) but they could be quite cold in February.

I'm going to take a wild guess and say you don't write Valentine's Day cards for a living.>

BINGO!

I just see this all as a two-way street - why can't a woman propose to a guy and ask these questions?

Not criticizing OP because he probably has done that and she said yes and go ahead and surprise me- but just in general why always the man should get this pleasure - I rather the couple sit down and both think of where the cherished proposal may be so don't think I don't see the romance in it all.

Again not addressing this to OP but to you in explanation of why if I did write Valentine's cards for a living in the way you expect.

Cheers and may the OP have a great proposal - lots of good ideas even though Milan and Lake Como in February would be amongst my very last choices but I guess anyplace can be romantic- not sure from where OP is flying or traveling to Milan from- but if a long way just for one day I'd suggest other places.

If you choose Lake Como, propose on the grounds on Villa Balbaniello. Take ferry from Bellagio to Lenno, then water taxi or walk to villa. Weather could be terrible- or nice.

do ferries run often in February? Maybe leave the choice until you see what the weather is like?