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getting started..need advice from travelers!

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Hopefully I will be able to get some help from advanced travelers out there!

My mom and I are trying to go on a trip around May/June and this is our first time out of the US. We have the list of countries we want to visit and a list of the main cities we would like to see. I've briefly looked up hostels to see prices, I've looked at guided tours, and other random things but I am stuck on where to ACTUALLY start. We would like to visit:
-Italy (Rome, Naples, Capri, Verona, Tuscany, and Florence)

We plan on this being a 2 to a 2 1/2 week trip. I guess my first question would be..where should we fly into? Should we start at the most Southern country and work our way up or start at the top?

And I guess my next question would be..once we figure out where to start (say southern country first) how should we plan our itinerary? I am currently a full time student at a University so all the help I receive will be greatly appreciated seeing as I don't have time to sit down everyday and try to figure this out on my own. Thank you all in advance!

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