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Germany and Switzerland in July

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Hi everyone! Looking for some advice from travellers. I will be travelling to Germany & Switzerland with my family. Our dates of travel will be July 8th - 26th (19 days). We're interested primarily in seeing historical sites (museums, castles, ruins), arts & culture and certainly a bit of nature! We are all generally in good shape and are able to walk all day long with no difficulties.

We are likely flying into Frankfurt, as it is the cheapest option (we are from Canada). We are considering flying home from either Frankfurt or Zurich, but we are open to suggestions. Here are the cities / sights we are hoping to see! Again, open to your suggestions!

Berlin
Rothenburg
Munich
The Black Forest
Rhine River Valley
Castle Neuschwanstein
Romantic Road
Baden Baden
Heidelberg
Trier
Zurich
Lucerne

I realize this list is quite ambitious. Could anyone help me out in whittling it down, or perhaps suggesting the best route?
We are hoping to travel by train. I've been looking into the Eurail Germany-Switzerland pass, but I've heard some tales of caution with these passes. Could anyone care to elaborate?

Finally, this is a bit of a sidenote, but I am hoping to extend my stay in Europe after this family trip for a few extra weeks on my own. I'm 22 and looking for a youth organization I could volunteer or intern with. If anyone has any leads, I'm all ears!

Thanks!

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