You sound like a potential candidate for the Virtual Regattas. I got involved with a few of these in the last year. You "virtually" sail a boat in a major race somewhere. It happens in real time, so if it's a one week leg from Cape Town to Rio do Janeiro,or whatever, that's how long it takes. Once you get into it, it's fun. You can spend as much, or as little, time with it as you want. You choose the sails, the heading, look at the maps and wind forecasts and start working on strategy. Looks like one starts April 10, and there is one underway now. You can join a race already in progress. The software will just place your boat somewhere in the pack and you start competing from there. You gain points thoughout the year for your finishes on the various legs. They give out prizes, and there are actual boats competing in some of these and you compete with the real time boats, too.
I have actually met some people online as a result of this, and now correspond regularly with some of them. You can email or PM other sailors in the pack.
I hope this helps your sailing jones.
http://www.virtualregatta.com/(We don't need it any more. We have our TI and Endless Summer.)
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Island life in the Devil's Triangle:
http://2gringos.blogspot.com/