I sailed in a couple of the Watertribe Everglades Challenge events that Dannyb mentioned. St. Petersburg to Key Largo, 3-4 checkpoints, but not a staged event. It is nonstop or camp as you can. Some people cruise it, the "challenge" is to finish within the time limit of 8 days. Some people race it. Fastest finish after 3 events was last year in just under 3.5 days. There are 4 classes ranging from kayaks to sailing kayaks/canoes to anything goes. Class 4 allows pure sailboats of any type as long as they are launched from the beach above high water. Access to one checkpoint requires negotiating a 9' fixed bridge, but that is part of the event. Auxillary propulsion (paddling) is allowed.
I sailed in 2 Everglades Challenges in a performance dinghy and did well. More importantly, I had a blast and extended my experience significantly.
Switched to a Hobie 21 this summer for the watertribe's Lake Michigan Challenge. Would like to get down to Florida again for the next one this coming March. There was an A cat in the event last year but the event really needs more cat entries. I contend that a 48 hour run is possible in a beachcat but have yet to prove that it can be done.
If you want to participate in a low cost distance event this winter, you should consider this event. It's a great group of people, a great route and guaranteed to be an excellent adventure!
George VS