A flexible skateboard may include a pair of direction casters mounted for steering rotation on a twistable one piece skateboard. A center section may be made sufficiently narrower than outboard foot support areas so that the board may be twisted by a rider to add energy for rolling motion to wheels in the casters. The center section may also be made sufficiently resistant to bowing and twist so that the skateboard may be ridden as a conventional, non-flexible skateboard. Wells may be provided to resist twisting and provide gripping surfaces on the board for the rider's feet.