A wheeled ski is disclosed that may include a flexible member. The wheeled ski may also include a first wheel assembly that includes a first wheel with a first-wheel first rotational axis and a first-wheel second rotational axis. The first-wheel first rotational axis and the second-wheel second rotational axis may intersect. The wheeled ski may also include a second wheel assembly that includes a second wheel with a second-wheel first rotational axis and a second-wheel second rotational axis. The second-wheel first rotational axis and the second-wheel second rotational axis may intersect. The first wheel assembly may further include a first axle coupled with the flexible member and a first rod that extends through the first axle. The second wheel assembly may further include a second axle coupled with the flexible member and a second rod that extends through the second axle.