Haha no i'm perfectly content, i just wish to broaden my horizons. Basically it feels like i've only ever seen one side of the coin having been a windows developer since graduating (I had some experience with Linux during university), so i'm just looking for some direction to take me to new and interesting places.

So with that in mind my goals are a little vague beyond what i've said above - I literally just to get exposure to some new languages, new tools, new ways of doing things. Maybe when i do try all these things I'll feel unsatisfied with my old tools (kind of a "never know what you're missing type scenario"); but for now it's purely just as a learning exercise.

Onto your recommendations: Do you know any excellent resources for learning python? Are there any good interactive online tutorials to my learning if Python was where i started? What are the web frameworks available for me to work with? I'm kind of interested in Ruby as it seems there are many great resources and tools to help you learn (i've just stumbled acorss Why's Poignant Guide and it's got me very curious, though maybe because of the haphazard, quirky style of authoring)

I expect Eclipse will be my IDE of choice since i have used it before and the paradigm is recognisable. Are there any alternatives IDEs that I should dip my toes into before i settle on Eclipse out of familiarity?

OK well I'll give you my personal perspective. For learning python, python.org actually has a very good tutorial. Then there is also http://www.diveintopython.net/ which is excellent. For web frameworks I use cherrypy which is very minimal. Seeing as you want to learn, I'd recommend you start with that as you'll get a better overview of what's really going on in the guts of a web framework. Emacs is excellent but I switched to Eclipse for its subversion integration.