I am intimidated by organizing my travel plans. I'm going

File: Baltic-countries-940x627[1].jpg (109KB, 940x627px) Image search: [Google]

109KB, 940x627px

I am intimidated by organizing my travel plans. I'm going to be taking my first solo trip to Europe after I graduate in December and I'll be trying to do it in winter.

I'm especially interested in taking my time with the Baltic countries and will hopefully make time for Prague (at the recommendation of countless people), Croatia, maybe Serbia. If I can, Italy and specifically Sicily.

I'm allotting myself 40 days and my budget isn't totally restrictive but I will be keeping things minimal by staying in hostels and not doing any superfluous shopping or eating out. I will likely be drinking a fair amount, though.

Is doing this in late December/January gonna suck ass? I'm from California and I am spoiled with the climate. I don't really mind cold weather, but if I want to meet other travelers my age, is it going to be harder in a less busy season? Is it even less busy? I like spending time in museums, if that is relevant.

Hopefully anyone else interested in these countries or needing booking suggestions could use the advice as well. I would like to fly by the seat of my pants but I also don't want to accidentally fuck myself. How far out in advance do you all book hostels? I guess my main uncertainty is that I won't know how long I want to stay somewhere and explore until I actually see it. Basically, I'm not committed to getting as many countries as I can crossed off of a list; if I love where I am I will have no problem staying put and really diving into the culture as an observer.