(September 11, 2011)
From my apartment in Navigli (the canals) it takes 20-30 minutes to walk up to the Duomo. There are three streets you use, and those three streets are probably my favorites in Milan: Corso San Gottardo, Corso di Porta Ticinese, and via Torino. FYI -- these streets also have great shopping.
If you walk north on Corso San Gottardo, it leads you to Piazza XXVI Maggio, which my roommate Angela and I called "The Triangle" for the longest time before we found out the proper name. ("Let's meet at the Triangle before dinner.") I mainly liked this street because it was unexpectedly convenient. It had banks, focaccerias, tailors, clothing stores (YAY FOR OVS!), a grocery store, and cell phone shops.
Once you pass the Triangle, you're on Corso di Porta Ticinese. There's a cute cafe called California Bakery, which is very Americanized so I suggest you pass and try something more authentically Italian, but you can get pretty good cheesecake and brunch food if you want. Also, if you keep walking north on the tiny sidewalk, there's an awesome gelato and crepe shop to your right. The street gets really narrow out of nowhere. The sidewalk is so tiny that it's pretty difficult to carry a conversation with anyone since it only accommodates one person. There's a random tokidoki that I've never really seen people shop in, but it must be somewhat profitable if it's still there. Last but most important--the Wurstel Prince guys were nice enough to let me use their bathroom once.
After passing under a random old brick structure/gate, you'll be at Colonne! This is not Colonne, Germany, but a church with a bunch of columns in front of it. It's a place where people hang out on summer nights and drink. Public drinking is legal in Italy, which is pretty awesome. My friends and I have met cool random people here and ended up becoming friends/hanging out with them. Oh, and I think there are some random people trying to sell weed here too. Besides that there's an American Apparel, and some other awesome fashion stores around the area (shoes and handbags especially).
A few steps north you will run diagonally into via Torino. You can also pick up my friend Aileen along the way--she lives on one of intersecting streets. This street is dangerous because of how much shopping there is. I so far haven't been able to pass by without buying at least one thing. List of my favorite stops: Pull & Bear, Bershka, Tally Weijl, Muji, H&M, OVS, Zara, and a lot of random affordable shoe stores. Once you turn the corner, you'll arrive at the Duomo!