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Feeling like I'm missing something for Berlin and Munich

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Hey everyone. Very, VERY, early stages of trying to convince a friend of mine to go to Germany in the fall of 2014 (yes, he needs that much notice as we are poor, young folk). We are in our mid 20s and major history buffs. I've found flights from Chicago anywhere from $850-$1000 which is pretty much what I expected. I should preface this with my major argument to him as Oktoberfest (late September, early October) and the purchase of beer steins since he is also interested in beers. Just preliminary research made me change my plans a bit. I thought we could do an entire week in Berlin and maybe 2 days in Munich for the festival. The problem is I hate coming all the way from Chicago to only visit 1 major city.

Judging from my preliminary list of "things to do" it seems like Berlin will take a lot less time than I thought. I used Fodors as well as the Berlin tourism site and made a list of my top sites. It seems the list can be done in 3 days tops as a lot of the things are "Ok, I see it, now what?" types of monuments. Here's my list:

Berlin Wall Victims Memorial
Berlin Wall Memorial
Berlin Wall Museum
Brandenburg Gate
Checkpoint Charlie Site and Museum
Neus Museum and/or Museum Island
German Historical Museum
Charlottenburg Palace
Memorial to the Murdered Jews of Europe
Soviet Memorial Treptow
Treptow Park

This is what I have for Munich so far from the same sites:

Oktoberfest (lots of eating and beer drinking!)
Nymphenburg Palace
Side trip to the Dachau Concentration Camp Memorial Site

Is it just me, or am I missing something? I've been to Paris so I'm trying to compare it to that. I had a list 2 pages long of things in Paris and we spent a week there and hardly saw it all.

I also really want to see a true, German castle such as Neuschwanstein but it seems far away from anything else we want to do.

My argument to him is that we should spend 3 days in Berlin (not including travel times) and 2 days in Munich as we can do the festival for a full day and a half and the sightseeing in a half day. Then I'd want to hit another nearby city. Yes, I'm one of those, "even if I just put my toes across the border I can say I was in Switzerland/Poland/Austria (you get the picture)!" So maybe 2 days in another nearby city.

It seems as though the train from city to city is a lot more expensive than i thought. I thought it would run in the range of $50 to get from Berlin to Munich but it looks to be closer to $200 for a train ticket one way. I looked at flights between Berlin and Munich and that seems to be close to $400!! Am I just ignorant/in shock?

I guess I don't really have a direct question. I'm more or less looking to get input from people. Maybe things I haven't thought of, etc? Feel free to ask questions etc. I'm supposed to present a powerpoint to him on February 1st of why we should go (don't ask) so I'll be checking back frequently. Thank you so much for any and all information. I love Fodor's and the community here and although I'm more of a lurker than a poster, I love reading everything everyone has to say.

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