Well you know Hobie makes something like that with their Adventure tri/kayak, it's got the foot pedal powered underwater flippers, a roller furling sail, no shrouds, easy to drop the mast to get under the bridge.

I wonder if anyone has tried using one of those in this race yet? My neighbor's got one but I have not sailed it yet. The sail is pretty small but I'll bet with a little work, you could add a small jib and maybe even some type of spinny, "turbo" it and make it a little faster.

http://www.austinkayak.com/products/747/Hobie-Mirage-Adventure-Island-Kayak-2010.html