I believe it is possible, but I see it as extremely dangerous if done with a tail dragger. The plane will tend to turn over so someone must hold it. That is when things can get dangerous, since the plane can blow over and hit the holder. A tricycle gear plane would be better, but only if no one is needed to hold the plane. I love flying in high winds and now have a special plane for that. It has a tricycle gear and is a twin boom pusher plane. A few days ago, during high, gusting winds, it cartwheeled on me during a landing, but ended up on all three wheels. NO DAMAGE. All controls looked good, so I took off again and did more landings.