Abstract: The present disclosure provides a skateboard assembly for providing a rider a surf-like experience having a deck having a bow, an aft, and a wheelbase, an aft truck and a bow truck each comprising an axle, the trucks disposed transversely beneath the deck, wherein the distance between the aft truck and the bow trick axles define a wheelbase, and wherein the axle of the aft truck has a length greater than the axle of the bow truck.