A copy of RosettaStone Italian, Two passports and two one-way plane tickets so I can leave the country and go to Italy with my girlfriend.
...Before I go though, I think I'd make a sojourn to New York City to buy that fabled Golden Opulence Sundae that everyone seems to know about.

Yes, that's real edible gold. And caviar in that there dish up top. And, evidently, very rare ice cream.
It costs $1000.
...And a huge library of 360 games, an NES, and a huge library of NES games.
...And a replica Weighted Storage Cube, if I can find it.
...And a much, much better laptop than the one I have right now.
...And a Selmer Paris tenor saxophone w/ form-fitting case.
...I'd probably keep the rest in my life savings.