I was just thinking about posting something related when I saw this thread. Has anyone tried either match racing or fleet racing?
I'm thinking of racing ships of the same class so the capabilities are the matched, setting a course around shoals or islands, then racing using yacht racing rules, with all of the jockeying for position ahead of the start line, penalties for right of way, etc. (no shooting!)
I've only just recently received my game and ships, and have been busy these last few days, so haven't even had some them all out of their boxes yet, so I haven't tried it, but I am eager to give it a go. It could be particularly interesting to try it with preplanning a second move, as in standard rules, or changes in sail settings as in advanced rules. Even more interesting to add a variant requiring changes in sail settings to be pre-planned as well.
There is a kids game called Regatta which already uses cards placed ahead of sailboats to determine movement, and it is fun, but it is still turn-based rather than simultaneous, it ignores wind direction, and although the lengths and positions of the arrows on the cards do vary slightly, all the card variations are really 90 degrees or straight ahead, so movement is not very subtle.
link to BoardGameGeek:
http://www.boardgamegeek.com/boardgame/65582/regatta