Tail high? Never risked that!
I used to sometimes spin the Chippy round and round in almost its own length (pivoting around a main wheel), a few turns one way, then the other. The joys of a fully castoring tail wheel! But I always held the stick hard back while doing it.
What aircraft do you want to do it in? Are you happy doing tail-up fast taxys? I used that a lot at Liverpool if there was a fair way to go on the ground. Tail-down taxying with associated weaving to see ahead is so much slower. I'd imagine what you want to do could be developed from tail-up taxying.