The first four minutes of this Joe Glickman video provides an excellent overview of surfskiing. The rest of the video focuses heavily on the competitive aspect of the sport, but recreational surfskiing is very popular and growing.
Intro to Surfskis and the 2012 US Downwind Championships
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(Olympic Sibling to Surfskiing)
Adam Van Koeverden - Canadian Olympic & World Champion
Traditional marathon boats bear some resemblance to K1 sprint kayaks, but the races are long distance and run over all kinds of water, on flatwater or through rapids, over small dam drops, and often include portages. In most venues races are open to a variety of boat types including surfskis. And the races often include portages.
South African Champion Sbonelo Khwela
(Single-Bladed, Stability-Loving Cousin to Surfskiing) More about Outrigger Canoeing
Kai Bartlett
Welcome to Surfski, Welcome to Adventure
each page of videos from around the world has approximately 12 entries (some have double ups for the same location or for the same downwinder). Although newer videos generally get added to the highest numbered tab list, these videos are not organized entirely chronologically - they get rearranged occasionally to maintain/improve variety within the lists.