Milan is a great base to get up to Munchen (if that's what the plan is - I couldn't tell if you meant Munich and Milan as two separate trips). You should take the train up through Switzerland and spend a night or two in Zurich. Alternatively, LCCs out of Milan offer some of the cheapest rates I've seen in Europe.
I went to Oktoberfest about 3-4 years ago, by myself. What a **** show. I was in Germany for other reasons and decided on going down at the last minute. Didn't have any reservations and ended up being forced to stay at this random youth campground on the outskirts of the city. It was cold and I ended up getting sick at the end of the time I was there (which I'm sure the alcohol contributed to) and had to take an express train to Frankfurt just so I could get a hotel room and take a hot shower. My suggestion would be to start making reservations ASAP (for both lodging and beer tents). And find some cool Lederhosen.
Also, you'll be surprised at the overwhelming stench of horse**** that's everywhere. So much horse****.
But so worth it.
I went to Oktoberfest about 3-4 years ago, by myself. What a **** show. I was in Germany for other reasons and decided on going down at the last minute. Didn't have any reservations and ended up being forced to stay at this random youth campground on the outskirts of the city. It was cold and I ended up getting sick at the end of the time I was there (which I'm sure the alcohol contributed to) and had to take an express train to Frankfurt just so I could get a hotel room and take a hot shower. My suggestion would be to start making reservations ASAP (for both lodging and beer tents). And find some cool Lederhosen.
Also, you'll be surprised at the overwhelming stench of horse**** that's everywhere. So much horse****.
But so worth it.