A wheeled sport item, such as a roller ski or a roller skate, is suited to be applied to the foot of a user in order to allow the foot to slide in relation to the ground according to a movement direction parallel to the foot. The sport item includes an elongated body associated with two wheels; a platform associated with the elongated body, defining a supporting surface for the foot; and a brake for braking the wheels. The item also includes a connector for connecting the platform to the elongated body, which defines a rotation axis orthogonal to the supporting surface, in order to allow a rotation of the foot, and a controller sensitive to the rotation of the foot for the operation of the brake.