My sis just got her sunfish- first sailboat ever. She's been out on it 4 times and this weekend she took it out for a 10 mile one way trip to a deserted island, camped for the weekend and sailed it back. Lost the rudder hitting a sandbar, had to get towed back after walking miles through marshes...whew...glad i wasn't there.
She's up in NC so it was also getting chilly (50s) so it sounded like one of those "cutting your teeth" kind of trips.
This doesn't really count, but I sailed 95 miles last Friday around a ca. 0.45 mile course (about 250 laps...).
Average moving speed was 25 mph; my GPS said the max speed was over 40.
No organized racing, but a number of us were keeping very close tabs on relative speeds/positions of our close competitors, so I'd say some of us were de-facto racing...
Passing the clumps of slower "cruisers" was a great test of boat (kart?) handling, especially on the narrow taxiway leg.