The summer before my final year as an undergrad in college, I downloaded and watched Star Trek: Enterprise. Realizing it was the first series chronologically, I decided to watch the entire series, in in-series chronological order. I had never watched Star Trek before, either, besides a couple random episodes from flipping channels.
Summer 2009 - Enterprise, The Original Series, Movies occurring before The Next Generation
Fall 2009 Semester, at 2 episodes per night - The Next Generation
Winter Break, 2009-2010 - Deep Space Nine plus appropriate TNG movies (6 episodes per day)
Spring 2010 Semester, at 2 episodes per night - Voyager
All that remains after Voyager is Nemesis and the 2009 movie. Probably during Finals week...
And I will have watched all of Star Trek in under a year!