NavList:

You may have heard about Volvo ocean race (happening right now). What you may not realize (i did not) is that you may join it from the comfort of your chair. The simulator shows positions of the boats that are actually in the race (as well as other 40000 virtual "racers") and the actual wind condition for the area. You need to set your virtual boat heading and which sails to use and the simulator will determine where the boat would go and update this information i real time. So if you want to change course in 2 hours you will have to wake up in 2 hours and change it. And do this for the next 6 months until the race ends. Unfortunately, there is no navigation component -- you always know where you are and where you are going, but I still think it is relevant.

http://www.virtualregatta.com/index_vvor2014.php

If you decide to join now, it will place you near the pilot boat, which is pretty far behind, but not all the way behind, and you still have half a year to gain progress.