I have a few feelers out for a singlehander.

Pete's got the GPS track for a 'round Sanibel course, although it does get a little skinny on the back side.

No reason a Charlotte Harbor circuit or Charlotte Harbor/Sanibel & back distance thing couldn't be worked out if there were any interest.

The Gulf Coast Sail Club and some of the big Yacht Clubs do have some regattas that they MIGHT let us in if we had a large enough contingent (and paid a hefty entry fee, I'm sure)

I guess the point is there is no shortage of things the fleet you propose COULD do, but it's really up to the creativity and effort of the fleet members.

How about hide a small keg of rum somewhere and leave clues along the route? Winner has to pour shots for all finishers. Loser has to take the trash back with them.