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Paris, London, and Rome are good starter cities if you've never been to Europe before, though they're of course more overrun by tourists than most other places you could visit. Will you be taking trains or planes between cities? If at all possible, I recommend at least staying a couple of nights in the Cinque Terre, on Italy's Ligurian (NW) coast... perhaps on your way to Rome.
Do you like sitting on tour buses with groups of your fellow Americans for the duration of the trip, however? I've done it (when I was 15), but wouldn't touch it with a 10 foot pole now. It really depends on how you like to travel, how comfortable you want to be, how much money you want to spend, how much organizing you want to do yourself (or if you want it all taken care of), etc.
In my experience, doing the "tour group" thing is actually much more expensive than doing it yourself (and you experience much less of local culture), but DIY is more of a pain in the ass if you don't like handling details and you'd rather stay a bit insulated within your own language/group.
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And think not you can direct the course of Love;
for Love, if it finds you worthy, directs your course.
--Khalil Gibran
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