If you love sailing, well then why not play a simulation on your computer. It is not like most folks have $100M to run an Americas' Cup campaign, so here's a quick search of what is out there:
- Sailing Simulator 5. Shipped in 2010 and there is a Windows demo. First hit on google, so got to try it.
- About.com likes something called Little Sailor for the Apple IOS devices and a historical Tall Ships Age also for IOS.
A bunch of these posts look very old, but someone really likes Virtual Skipper 5 and it looks pretty cool.
Finally, SailX seems to come up a bunch too.