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I currently use the third canoe of my own that I have rigged. The very first canoe that I ever sailed was one of the 17ft Grumman aluminium canoes at an outdoor activity centre where I used to work. The centre had a Grumman lateen rig so I tried it out with an old dinghy centreboard G-clamped to the side - it all worked surprisingly well and I was hooked!
So I rigged my own Old Town Discovery 158 with a small gunter-rig sail left over from a long rotted small dinghy and sailed that for several years. Then came a Mad River Explorer and several versions of sail and rigging, from another gunter to a balanced lug, both sometimes with a mizzen and/or jib or genoa depending on wind strength on the day.
I started using Solway Dory gullwing outriggers with that canoe and I am now a convert for their use on open (and especially coastal) waters in boisterous conditions.
My latest canoe is an Old Town Penobscot 186 in royalex plastic, so a fairly large craft but it's great for sailing and is good for load carrying, especially for two of us on camping trips.
The canoe is fitted out with a leeboard thwart that fits onto the portage yoke/thwart, all in ash and strengthened with a hidden alloy angle brace. The solo paddling seat has an extra wide webbing area so that it is comfortable to sit anywhere on it when balancing the boat in light to moderate winds; when it gets a bit breezier I can sit up on the gunwhale to hike out. I've fitted some ropes under the buoyancy bags to hook my feet under as toestraps if I'm really going for performance.
The mast thwart is a fairly substantial affair (custom made for me by Dave S at Solway Dory) with a plywood box to brace against the significant sideways loads exerted by the 5 square metre bermudan rig (also by SD). The mast locates into a socket bolted to the hull of the canoe (using bolt holes already made by the previous owner, otherwise I would have bonded the socket in place) to cope with fore-and-aft loads.
I've added some side benches recently (2011) that make it much more comfortable to sit out in good breezes.
I've made a video that shows all these features and more, which is probably more informative than just a few stills: