I spent 3 months living as a student in Milan and, to be honest, I didn't like it. I found it dirty, ugly, unfriendly and oppressive, and expensive to boot. This did at least give me the motivation to seek out the best places to drown my sorrows, and I will be sharing some of that knowledge later. I've since returned though, and have learned to appreciate some of the good things this sprawling city has to offer.
Milan is an industrial city in the North of Italy, easily accessible by Malpensa Airport and then a short bus ride. It is also well connected to the rest of Italy and the countries to the north by train, and so however you arrive you will probably wind up at the stazione centrale. It's worth looking at this building, which is an incredible example of the fascist/futurist architecture favoured by Mussolini. Keep a tight hold on your wallet, pickpockets abound here.
The most famous building in Milan though, has to be the Cathedral in Piazza del Duomo. Take a tram or underground train (public transport in Milan is excellent, don't even try to use a car or taxi.) to "Duomo" and spend some time soaking up the cosmopolitan atmos - Milan draws tourists and fashion industry professionals from all over the world, and a large (by Italian standards anyway) immigrant population . On the whole, Milan seen from ground level is not particularly pretty, so walk round to the left of the cathedral where you wil find stairs (and a lift) to the roof where, for a few thousand lira, you can take in the most spectacular views in the city.
You are now on the outskirts of Milan's fashion district. Keep wandering away from the piazza and sooner or later you will find little side streets crammed with designer outlets, each more exclusive than the last. Unless you are planning to really impress someone with the size of your wallet, don't buy anything to eat or drink within half a mile of the cathedral - you are unlikely to find anything really worth eating. If you really must eat go to the AutoGrill or (If desperate) one of the dozens of McDonalds in this area. While the food is no better than anywhere else locally, at least the prices are acceptable.
For really good food, there are only two restaurants I can recommend - and sadly I can't remember the name of either - however they are both on the same street and easy to find: Go to Parc Solari to the South and West of Duomo, and head for Via Montevideo. Before long you ought to stumble upon an excellent pub called Murphy's Law. Stop here for a pint and a chat with the (Irish) landlord, then head into one of the two restaurants on the same street. You will pay a fair bit of money at either one, but the food is truly magnificent.
If you prefer to cook your own food, the market near Piazzale Piemonte and Piazza Sicilia is unmissable. You can get all your genuine italian speciality meats and cheeses at market prices. For clothes and other goodies at market prices, try the Monday morning market along the South bank of Milan's main Canal.
This canal, and the canals around it are all about 15 minutes walk south of Piazzale Duomo, and is the real heart of Milan's nightlife. There are more pubs and bars along here than you could care to mention, all of various quality. I recommend you try as many as you can and pick your own favourite. If you should stumble across it in this (I can't direct you, sorry) go into Pogue Mahone's - A really lively pub with atmosphere steaming out of the windows. Another good one is The Old Fashioned Cafe, which is between Piazza Cadorna and Parc Sempione, hidden round the back of a building which looks very much like a theatre. They used to (and still might) do wicked international nightys of a Wednesday. Turn up early in order to get food and drink cheaper. Don't bother with beers, go for the killer cocktails.
Parc Sempione is also attached to the lovely old Castello sforzesco - it's free to go in and look around, as is the museum, and it's a nice place to sit and eat lunch. Be prepared for the stray cats though.
Finally, try to plan your visit to coincide with the festival of San Ambrogio. Every year, in November or December, a whole village of market stalls fills the streets around the private university (La Cattolica). It's nice to wander round the stalls with a cup of mulled wine picking out unusual Christmas presents.
Oh, and if you are ever looking for rented accomodation in Milan, be very, VERY careful.
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