I'd be happy to share some info. I haven't been here long and have only been in charge of our little club for a couple of years but here goes:
The original Fool's Regatta was started by a couple of folks with a large trimaran and a large catamaran 18 years ago. The challenge was thrown down on the South side of Providenciales to sail from Sapodilla Bay to Pine Cay's north side, drink a rum at the bar and sail back. I really don't have much more info than that other than the original races were traditionally held on or around April Fool's Day.

Over time, more sailors joined in but the race was predominatly big boats until the interest began to wane and the Provo Sailing Club got involved. The big boats still raced but as you can imagine the people left on the beach didn't have much to look at. So the PSC's thing was to get the Hobie Waves from their club (3) and get all the other resorts along Grace Bay to send a boat and sailor (upwards of 10) Mike Rosati's 3 boats from wind surfing Provo and hold some open racing off the beach while everyone waited for the big boats to return. A casual race fee was charged and a number of races were held and eventually perpetual Trophies were created (the Bent Prop award for biggest hardluck story, the Governor's cup for the best sailor out of 3 races, The Resort Challenge cup for the resort sailors etc etc) and the biggest prize was a case of donated Mount Gay rum to the winner of the big boats which has most often been a very fast Trimaran named Minx owned and sailed by Mike Robertson who I believe was one of the originators of the Fool's Regatta.

So, this thing has morphed over the years into more of a party on the beach with some sailing thrown in rather than the other way around. However, the goal each year is to raise funds for a charity or something good and this year the funds are being split by our Collegiate Football club who are sending their kids to Costa Rica to play in a tournament their representing Turks and Caicos. They are doing the food/drinks and will be sharing the proceeds with Nissi House Orphanage on Provo who are in desperate need of funding always.

That said, there is still all sorts of fun and the Wave sailing is colourful (due to the amount of "paint swapping". This year the kiteboarders will do a downwinder from Leeward cut to the Bight to add to the colour on the water. The native sloops will be doing a race or two hopefully if they get organized and the Waves will take anyone who wants to pay a small fee to use the boats gathered on the beach. We are also trying to organize a corporate Tug-o-war challenge of teams of 5 to keep the beach events lively. And there is music and dancing in the sand until the light and/or beer runs out.

So there you go a rather windy account from a relative new guy (4 1/2 years on island) who didn't know how to sail until I got bitten 3 years ago and now I'm trying to justify the shipping costs of getting a NACRA here (not to mention the cost of ownership and duty once it gets to the island). So, for now, our little club keeps us busy.

If you are still with this post and interested, go to:
http://provosailingclub.blogspot.com and read a bit more about us. Sorry that I haven't been very prolific on the posts. Hard to keep all irons in the fire red hot.
Happy Sailing!