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Itinerary Help for France/Germany/Italy for how long?

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I'm taking a trip with 3 friends and we are all in are mid twenties. We have 2.5 weeks planned to go to Europe in September (the non-tourist season) and are having trouble planning how many countries and cities to see. We generally want to backpack and take the EuroPass and at least see two of the countries. What is the best route for this trip? Cheapest/easiest cities to fly into/out of for open jaw?

We generally want to see Rome, Vennice, Pisa, Paris, and Berlin, but are open to ideas/suggestions.

Any advice would be greatly appreciated! We are all excited about the planning of this trip but just can't seem to put all the pieces together.

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