Tillerman recently wrote an excellent review of Second Life and how it can be used for bored sailors in the winter. He pretty much convinced me that I really didn't want to bother with the program.
Because there's a better solution for virtual sailing. It's called the Sailing Anarchy forums. All it takes is a short registration, a few days of putting up with flaming, and then, presto, you can be a virtual rockstar super-sailor. You get to put down anyone who isn't as good of a sailor as your virtual self, and flame those that don't have as nice of a boat as your virtual yacht. You can claim victories in your virtual regattas and incite flame-wars with your virtual enemies. It's better than sailing.
I've never gotten into the flaming aspects of it but sure as heck enjoy reading them. Go virtual.