While sitting on the stairs of the Duomo in Milan waiting for a friend to get off work, a guy seated next to me struck up a conversation. In our five minute exchange he mentioned he was staying in the city for ten days. What he would do to fill up the week and a half in Milan was beyond me, especially since I had seen most everything in one day. The four days I was spending in the city would have been too long, had I not been visiting Anna. But even then, I supplemented it with a day trip away. So I thought, and thought, about what there is to do in Milan and this is what I came up with:
Go inside the Duomo. It may not be the most spectacular Italian Cathedral you've ever been inside, but it's beautiful. There's even an option to walk along the roof, which is quite a treat since the outside of the building is near the top of the list of most spectacular Italian Cathedrals.
Shop. Shop on all the streets behind the Duomo, along with all the ones leading towards the castle. And if you're there during sale season, unless you're a backpacker trying to get by on $15 a day, you can even do more than just try on the clothes.
After walking towards the castle on your shopping extravaganza, visit the castle. Not that it's very exciting, but you really don't have much else to visit, so you might as well take a peek.
Check out Leonardo da Vinci's Last Supper. You may never have had a yearning desire to see it, but go. Tours are given daily, in 15 minute intervals. Reservations must be made in advance, but you could be lucky by showing up the day of and stand in line behind a lady who asks if there have been any cancellations, even though signs dotted around the visitors room say all tickets for the day are sold out. The person behind the counter may tell the lady there happen to be a few openings available. That's when you pipe up and ask if you can be squeezed in too. The wall sized painting (not a fresco) will blow your otherwise blasé perspective of the painting out of the water. Reproductions can't give it justice.
Laugh at the rain. Laugh at it because the droplets are so large and so spread apart you can avoid every one that falls. That is, laugh until you must run and hide yourself against a building when the rain gods of Milano grow angry of your mocking and send water gushing down like a waterfall for hours, adding in giant balls of hail for emphasis. Just pray that the shop owner near the window you're squeezed up against waves you inside to wait it out.
And when you can't wait any longer for the rain to subside, make a mad dash for the California Bakery where you can have a nice cup of herbal tea and some of the best cake you've had in a long time while you dry off.
Also... don't miss the Italian Happy Hour. Bars all over the city offer a free buffet from 5-9pm with the order of one drink (alcoholic or non).