I'm with Dave on this one, too! Florida has a number of great venues for both fresh & salt water sailors. Between the Keys, Miami, Ft. Lauderdale, Cocoa, Daytona, and St. Augustine on the east, and Tampa, Clearwater, Dunedin, Pensacola, and even Naples on the west, it's hard to find a weekend with NOTHING going on!
I'm going to say that so far, Jetty Park Ocean Regatta (JPOR) has the best logistics, food, smack-talk, and venue. The beach access is normally restricted, but they planned it so well that there wasn't a problem. Now if we could just get those dang cruise ships to stop with the swells...
Also putting them on top is that all those NASA guys are pretty good about calling the weather, and got us on the beach before all that bad weather stormed over the horizon on us!
I've yet to sail St. Augustine, but it should be fun, as the I-20 state champion will be determined that weekend, and I have to pay my dues/respects there...
As for distance stuff, it would be Key Largo Steeplechase for it's competitiveness and overall challenge, and maybe the Miami Key Largo for it's sponsorship and attendance. The only drawback to the MKL race (besides the price) is that they hold the skipper's meeting and award ceremonies in such a way (a week later) that the out-of-towners are not in a position to attend.
A very close second would go to Pensacola (only reason it's not tops is it's about 10 hours drive from my house) and the Tampa area (Tampa Bay Cat Sailors really put on a show - only drawback is the weather can be quite a bit more flukey there).
I'm hoping that they will eventually design a steeplechase around Egmont Key in Tampa Bay. Starting/finishing at Davis Island YC or something...