I'm not sure how strong you want your encryption to be. But maybe an encrypted archive (rar/winzip/7zip) is an option for you. The howto of extracting such archive files is well known, and easy to explain if needed. There would be even an option to make it self extracting.
The latest version of RAR would be RAR3 which supports AES encryption with 128 bit key length for example. File data aswell as the headers will be encrypted.
This way does give up security for ease of use, but it's still rather hard to "crack" such an protected archive. But do be aware of password crackers that are designed to brute passwords on such archives...