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First Trip, Destination: Europe - The Perfect 2-Month Itinerary

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Here I am, 25-years-old, planning my first trip to Europe (really, my first trip out of the United States, but let's pretend I'm not that lame) and I desperately need your help. Here's what I want to get out of my trip: to expand my worldview and understanding of different cultures, because I've spent most of my life in New York and feel very limited; also, to see things that are (expletive) magical. Also also, being Italian-American, I feel compelled to go to Italy. These are really my only requirements - all suggestions and recommendations will be taken into consideration; obviously, explanation/substantiation is incredibly helpful, as I'm just about as n00b as they come.

Let me provide a brief summary of the circumstances surrounding my trip, which will most likely take place between July and September: A) I'm telling the school at which I teach (in Brooklyn) that I won't be returning next year; B) I have $8K put away just for this trip, but this has to include all of my expenses, and C) I won't be putting a lot of effort into getting a job so that I can spend ~2 months in Europe without stressing over a return date.

Here's what I need from you: everything. I've done my research, but there's only so much you can get from a smattering of blogs. I want to hear from a chorus of seasoned travelers. What would an ideal ~2 month (or ~$8K, if you want to think of it that way) trip to Europe look like? I ask you to write as if it were to a younger inexperienced version of yourself - Where would you go? What would you see? How would you do it? I know I will continue to travel in the future, so I am NOT compelled to skim over a bunch of places just to say that I've been there - I would rather return home with a much better understanding of Europe and its countries and its cultures, and myself. Quality over quantity. The rest I put in your hands.

Of course, any useful tips/hints/tricks (from booking travel from New York to wherever, to when to buy a Rail Passes and inter-country travel, to whatever other things you can think of) are MORE than welcome. I thank you all in advance for your help.

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