Shame on you! A Nacra sailor looking for help from a Hobie fleet! And no, the fleet folded years ago.
Sailing in Pine Island Sound with a board boat is all but impossible. It is one enoromous grass flat with an average depth of 1-2 feet. Very often, at low tide there isn't even enough water to float the hulls. I've often run aground on a Hobie 16. Granted, there are channels and other areas where you would be able to get the board part way down, but your best (only) bet is to sail in the Gulf.
The only useful launching area is at Punta Rassa,just to the Gulf side of the Sanibel Causeway Toll Plaza. This too is guarded by grass flats and sand bars, which are exposed at low tide.
The ramp at Pineland is in very bad repair, where the concrete ends there is a substantial drop off due to erosion. The ramp is usually covered with grass and other detritus, walking on it is difficult because the surface is very slick. The channel is not lined with rocks, it is lined with boulders, some as big as a car. The grass flats to either side are 1-2 feet deep and the channel itself is very narrow. There is no adequate launch area, you would have to step the mast with the boat on the trailer. I have done this with a Hobie 16 several times and once with a hobie 18. Wear tennis shoes, when you run aground, just step of the boat and walk it to deeper water.
The Bocilla Club has a ramp at Bokeelia, but no place to leave a trailer.
There is a public ramp in downtown Punta Gorda, but you'd have to sail the length of Charlotte Harbor.
I think Pineland is your best bet, once you get out of the channel, work your way to the North into Charlotte Harbor and be very careful inside Boca Grande Pass it can get very rough when the wind and tide are against each other.
On the bright side, sailing in the Gulf is just gorgeous! And all of Upper Captiva is one big pristine, white sand beach. Same for Cayo Costa, the next island to the North, which is mostly a State Park. Also, when you do run aground you're not likely to suffer any damage, just step off and go for walk. Lots of interesting critters in the grass.
One of my fondest sailing memories involves the ramp at Pineland. I was ghosting along in the shallows, trying to work my way into the channel. It was near sunset, the water was like glass the wind was so light the boat barely left a wake. I was standing near the forward cross bar and looking down discovered I was surrounded by a school of Red fish! One, about twenty pounds, was tailing between the hulls, I could easily have reached down and touched him! 'Course, I guess you had to be there.
