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Itinerary help? 5 weeks in Central/Western Europe

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Hello, travel gurus,

I'm a very lucky person. My graduation present is five weeks in Europe and an Interrail pass. I want to make sure I make the most of my travel time, so I'm working on an itinerary. I plan to go with a group of three other girls, all of whom are from Germany. We will all be 18. We have a long list of places we'd like to see. Here's the first draft of our itinerary:

Start in Frankfurt then:
-Venice
-Florence
-Milan
-Cinque Terre
-Nice
-Marseille
-Lyon
-Paris
-Brussels
-Amsterdam

I also want to see smaller towns like Manarola in Cinque Terre and find a way to visit Prague and Vienna.

All four of us are concerned that we won't get to spend enough time in each city; we want to cut down our list. So our streamlined itinerary could look something like this:

-Frankfurt
-Venice
-Vicenza
-Florence
-Cinque Terre
-Paris
-Amsterdam

With Prague and Vienna somewhere in there. Any suggestions for how I can fit these in? Only one of my friends and I want to go.

Is this realistic? Would we be able to easily fit in any of our other destinations from the first list? I would appreciate some general travel hints as well.

Notes:
All of us have experience traveling without an adult. My friends can speak some French, English, and of course German.

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