: It's been done on my myriad Dyson baidarkas, plus on my own
: Chuckanut 15 kayaks, and also on generations of Kleppers and
: Folbots. There are two different varieties of kayak sailing,
: basically - downwind only, and "real" sailing.
: Downwind only (beam reach and below) rigs are common, and easy -
: all you need is some variety of sail (and there are many!), and
: a paddle to steer with. The stresses on the rig are minimal, and
: the rewards are often great.
: "Real" sailing - i.e. rigs that can go upwind, too - are
: a whole different animal. You'll need some sort of leeboard,
: daggerboard or centerboard, plus a rudder - plus some beefing up
: in the frame area where the mast thwarts will be.
: But, when you rig a kayak to sail upwind, you could often paddle
: upwind just as fast! Sitting down in a narrow kayak severely
: limits your ability to use your weight to counteract the force
: of the wind on the sail - meaning that you will get overpowered

Check out the Tasmanian kayak sailors. I think they are at the cutting edge of kayak sailing. No leeboard, but rudders are necessary...their small sails apparently point upwind pretty well, although in any real wind I would think running is the safest option. In fact, as I understand it, the Tasmanian paddlers use their sails for safety...to get out of weather ASAP when it turns bad. Tasmania is kind of in the path of the roaring forties, so they need a safety valve. I heard there are some club sanctioned trips that require sails for safety. I truly don't think a SOF kayak needs any special reinforcement beyond what a "normal" boat would need. Kayaks are skinny and tender enough that there is not much torsional force from the sail. I think many Tasmanian sails are deck stepped with shrouds.

: early and often. The wider your kayak, the better (in that
: respect), and that's why CLC has a sail rig available for their
: kayaks that features outriggers that you attach to the main
: hull.

: Check out Todd Bradshaw's superb book "Canoe Rig: The Essence
: and the Art" for tons of info and great illustrations.