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maxa said..
It does take a lot of wind to get a land board going on grass . Harder grass and more Tyre pressure the better.
Works better on hard ,low tide sand. Tennis courts would be good, hard on the body I would expect
Winging on asphalt with a skateboard is pretty easy and good fun, helmet,gloves and knee/elbow pads are a good idea od course.
A small(4 or 5m) wing,a longboard with 70mm wheels and 10knots max will do the job fine on a decent surface.
Do not go too fast at first, wheels have very low resistance on a smooth surface,depower as needed and practice transitions a million times.
Do not expect miracles though, it helps but it will not translate into success in the water just like that.The foil is way more sensitive to weight shifts than a skateboard.The critical fore/aft foil balancing act is non existent on wheels.
But very good for wing handling,carving etc.