I have tried the wing skate sails on in line roller skates at low speeds on asphalt. It felt a bit uncomfortable because the skates (self-made, not very light running) made more resistance and were more difficult to turn than my ice skates which made it a bit difficult to counter gusts. See picture.
With more training and better skates it would probably be more comfortable.
For land sailing on tidal beaches and dry lakes, which we don't have in Sweden, you could use in line skates, maybe with big wheels under the foot (diameter of 30 cm is probably no problem if you use alpine ski boots, as skate sailors with high skates do), a skate board like platform or a bicycle.
The wing would probably be faster than a small land yacht or a buggy (a land sailer pulled by a traction kite.) On ice the wing skate sail has beaten big USA ice boats, Skeeters. Maybe it can also beat large land yachts.
I don't know of anyone who has tried the wing skate sail on water. Used on a sail board or foilboard I think the maximum speed could be increased several knots as you get rid of the air resistance of the sailor. See Youtube: One of a Kind race with: Stand inside wing, Platform with wind surf rig, Kite sailor, Traditional Swedish skate sail and Skimbat sailor: https://youtu.be/gmJc8m3XICI See also Wing sail VS Kite sailor on ice: https://youtu.be/VY3xsgJaIrQ
There is the risk of drowning when you crash which can be reduced with a face fixed emergency air supply.
The wing skate sails have been tried with skies on snow and it works OK. Skies on snow make greater resistance than skates on ice, and as we usually have good ice to sail on our sailors prefer ice sailing.
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