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Roger Derby
 
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Would you be reinventing that round thing with an axle thru it? Sailing
canoes have been around for several times longer than I have and that's a
long time.

A typical rig would involve a low lateen sail, lee boards, a rudder
controlled with a line running around the boat and terminating to a
cross-wise tiller on the rudder head. No outriggers.

Putting "canoe sailing rig" (without quotes) into Google got over 51,000
hits including plans and how-to books.

It is a fun thing to do.

Roger

http://home.earthlink.net/~derbyrm

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I have an old 18' Grumman aluminum canoe that I grew up with canoeing
most of the rivers in FL. It has enough room to carry 4 people or
to carry camping equipment for 2. It seems like it might be possible
to design a good sailing rig for it. Maybe use a lateen rig,
outriggers, retractable leeboards instead of a dagger board, design
a good rudder.