24M; Europe backpacking trip (Eurorail) (June 23-Aug 1). Amsterdam-> Berlin-> Prague-> Munich-> Italy-> ferry to Greece and hopefully http://Mykonos..Tips/advice/must see and/or not see places!

As mentioned, I am a 24 year old male (And have been told I’m an attractive and fit Texan) traveling to Europe, leaving June 23rd (thought my grandma used frequent flier miles and could only get my return flight on Aug 12...But orientation for my dental school is Aug 5th, so I will have to find a way to leave early). I purchased the global Euro-rail pass, and my plan as of now is (I should also mention I have a round trip ticket from Texas to London, and a one way from London to Amsterdam, so where ever I end up after around 5-6 weeks I can just fly back to London...and hopefully figure out some way to get an early flight home without buying a new ticket). My plans are: Amsterdam-> Berlin-> Prague-> Munich-> Italy (starting at Venice-> Florence-> Rome) -> ferry to Greece and hopefully Mykonos. I am looking for helpful tips and advice on solo backpacking across Europe (I've done a bit of research: will get a travel belt, carry my backpack in front of me at railways and major metropolises, obviously use my common sense lol, and am thinking I will use a debit card and take out ~200USD from ATM's at a time to spend. (I am slightly limited on cash, but I have saved a few grand from working, though I’m looking to stay in hostels and possibly couch surf.

Looking for advice on:

1 What to pack (like 3-4 t-shirts, 1 long sleeve, 1 jacket, 2 pairs of jeans, socks, underwear, a camera [no cell phone], passport [with a copy of it just in case], debit card, my cowboys boots, an extra pair of shoes?)...anything else?

2 Must see places, places to avoid, important tips and advice, where to go online to find more info, places online to find couches/hostels, etc... I do want to do a fair share of partying (I don’t smoke, or do any crazy drugs; though I have experimented with a few minor ones that were fun [and I'm not against my friends who smoke or do crazy stuff, as long as they're not messing up their life, or stuff like that]), but I would also like to stay safe, meet interesting people and experience the culture, as well as visiting culturally significant sites/monuments/museums. And get advice on how to avoid getting scammed, ripped off, find good deals, and most of all..... HAVE A BLAST AND MAKE IT A TRIP OF A LIFETIME (before I have to settle down for dental school:)