Here is my rough guide to getting Jekyll running on Mavericks. I plan on updating this post in the future to include a description of each command.

Download and install Xcode
$ ruby -e "$(curl -fsSkL raw.github.com/Homebrew/homebrew/go/install)"
$ curl -L https://get.rvm.io | bash -s stable --ruby
$ sudo gem install jekyll
$ sudo gem install rdiscount
$ jekyll serve --watch