Oktoberfest is an obvious win,
well too bad it's only in the last two weeks of September

You can buy a bavarian Maßkrug all year 'round though.
...as is a trip to Athens and Rome. Venice, eh, I've heard nothing but bad things about. Plus there's a great DoD ski resort in the Bavarian Alps I was going to look into so I can show off my mad board skills.
best ski resort in the bavarian Alps: Nebelhorn-Fellhorn-Kanzelwand. You can ski around three mountains that are all interconnected through skilifts and cross the border to another country at the same time (Kanzelwand is already austrian). Since it's really big, it's not too overpopulated on the various trails and there's something for every level of skiing experience (Fellhorn summit Buckelpiste is pretty demanding... beware

) plus it's only a 30 minute drive to two other less known (mainly to locals) and smaller ski resorts in Immenstadt (Alpsee Skizirkus) and Gunzesried (Bergbahnen Ofterschwang-Gunzesried) if you want to explore the area a bit (which is btw beautiful and ehm... yeah I grew up there

)
Personally I prefer this ski resort over the Garmisch-Patenkirchen (Zugspitze) or Bayrischzell (Sudelfeld) areas, since those are imo overrated and therefore overpopulated :/