I started playing around with gnupg. I've posted my public key for anyone who might be interested.
I had originally just installed the base, command-line app as that is what I was familiar with, but winpt looks like a pretty good, full-featured gnupg GUI. I'll be using that from now on.
Along the same lines, I also downloaded enigmail, a Mozilla Thunderbird extension that allows you to send and recieve gpg encrypted/signed messages. All in all I am very impressed with the polish and integration the Firefox and Thunderbird have achieved. Despite the fact that I'm a hardcore microsoft fanboy, I have fully converted as far as those internet/email tools go. I even found that you can have a calendar in thunderbird :-)