Thanks! I do a lot of yoga. I must warn that there is a lot of buildup to learning how to do a headstand correctly. There is great danger to the neck and spine if done improperly so DISCLAIMER: If you do not already do headstands in your practice,
do not try this at home. Go to a yoga class and ask the teacher to assist you. Once you're comfortable, it's a matter of learning how to get up with both feet stuck together (start on your knees and use core strength). On a paddleboard I don't even know how I do it, the first time I just copied my yogi girlfriend and was like WTF it worked! Years of surfing somehow transfers when you're upsidown I guess.
Technically speaking though it should be possible in a silicone tail. I don't have one yet but I imagine one could build up to the weight until it's comfortable. Doing it on beach sand would lessen the pressure on the top of the head.
What I really want to get to is Scorpion Pose, this would be the bomb in a tail: