Neatness

Sailing canoes were popularized by John MacGregor and his adventures in his Rob Roy sailing canoe in the 1800's and the use of them for cruising and racing became very popular in the 1880's until about the 1920's. There are online versions of his book available online for reading if you're so inclined - A Thousand Miles in the Rob Roy Canoe on Rivers and Lakes of Europe. They're still used for racing and cruising, but the popularity waned and has slowly been coming back. Now these are decked sailing canoes, not open canoes and are a bit more seaworthy than the open boats.

W.P. Stevens was a proponent of sailing canoes who wrote about, designed and built them. There is some debate, but it appears that Mr. Stevens built a boat called Yakaboo that was sailed by Frederick 'Fritz' Fenger to the Caribbean. He wrote a book called Alone in the Caribbean about his journey.

At any rate, an engineer named Geoff Chick decided to build a sailing canoe in the tradition of the boats of the 1880's using resources that were available to him on the Web. He has written an interesting blog on the subject that is well worth the read. He utilized very modern tools and materials, but built what I consider to be a "traditional" design from it.