Here's what I propose now that I think about it. How about
"2 Days 2 race?"
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It's time for another Pirate Report event! This time ye'll be sailin' in a race for fame and fortune, in two different races!
Saturday we'll be holding a regular, safe, friendly race around the islands of Port Royal. Go out, buy a light sloop, and get ready to race!
Sunday, things really heat up when we have an action packed, danger ensued race from Port Royal to Tortuga, then off to Cuba and back! Still light sloops, team's are welcome if you think you can't handle those ships beyond Cuba alone!
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Of course, that's a sketch of the races. Teams would be an option at their own risk, and to be fair each race would pay the same turnout. ^^