That’s a nice long trip.  Good for you.  Railpasses are the way to go for first timers – they make it simple to alter plans and you don’t have to stand in line, etc.

A 1-mo eurailpass would work in theory; start your trip in England, find your way to Ireland, boat to the continent after 5-6 days on the first day of your pass. Finish your pass in Germany, then buy your tickets additionally for Poland, fly home from there.  But I wouldn’t do this.  That’s an incredible amount of surface travel even for your dates and you’re going to spend an ungodly amount of time on trains and boats when your goal is to see Europe, not the inside of a train.

The truth is you really can’t do the whole continent in the time you have and still have an enjoyable trip.  Note that you said “first time backpacker” – meaning you’ll be back.  You really need to pare this down into something more manageable.

It’s mighty hot and crowded in southern Europe in the middle of summer.  At a minimum, I’d suggest that you eliminate Greece this time, which requires too much time on the ground for sure, and maybe Italy.  Axe Austria for sure too and be happy with Switzerland (or maybe just stop in Salzburg from Germany as it’s right on the border.)    Even that leaves you with seven countries and only about 5-6 days per country.  London, Rome and Paris require about 5 days each.  Still a lot to accomplish.

Anyway, then you could look at a selectpass option for 5 countries – Benelux, Germany, France, Switzerland, and Ireland.  If you keep Italy, then drop Ireland from your 5-country pass and get there instead on a cheap flight with Ryanair from one of the other countries.

Most night trains are covered, but not sleeping berths. 

Hope I didn’t shatter your travel dreams.  But you’ll probably have a better time if you slow down a tad and see stuff.

Haha, I forgot to mention that my plane ticket is for athens on arrival and I’m departing back to the states from Dublin. So either way I have to take this route. On average I plan on staying in one place for 3 days (Do all the touristy stuff). A couple of places, like austria…poland….ect…I’m just staying for maybe a day to check out the sites there and move on.
 
My plan is to get touch on every place I can, and then I’m taking another 2 months off next year to go to the places that I liked the best. Not sure if this is the wisest way to go about it.
 
Thanks for the input though, keep it coming if you more advice.

Then you’ll probably want the 1-mo Eurailpass.  Drop Poland and Austria to streamline, spend last 9-10 days in the British Isles so you can use the pass to reach Ireland.  If you’re headed for Rome, Florence, Venice or Paris, plan for tourist overload; reserving a bed would be smart.