RubyForge offers a very nice and easy One-Click Ruby Installer to get Ruby installed on your Windows system. I used it and it worked wonderfully. I next used the built-in gem command to install the latest Rails. Again, great. No problems.
Next I installed Cygwin so that I could use the familiar bash shell to run rails commands and use the vim editor to edit code and so forth. Oops. Not so fast there buddy. When I tried to run the rails commands in the Cygwin bash shell, I'd get errors. For example, using the Cygwin bash shell, executing the "rails" command yields:
c:\ruby\bin\ruby.exe: No such file or directory -- /cygdrive/c/ruby/bin/rails (LoadError).
In the end, to fix this issue, I uninstalled the one-click Ruby installer, and installed the Ruby that comes with Cygwin. Then I downloaded the latest RubyGems to a Cygwin directory and unpacked it. Ran ruby setup.rb to install. Now use the gem command to install rails. Phew. That's better.
Here's info on an alternative Windows setup for Rails using Eclipse: http://www.napcs.com/howto/railsonwindows.html.