A personal transportation device having first and second elongated foot support member that are arranged substantially in parallel and approximate to some extent the experience of skiing. The lateral distance of the foot support members may be adjusted. Biased-direction caster wheels may be provided that permit propulsion from side to side movement as well as kicking off and other propulsion techniques. Tiltable steering assemblies are disclosed that may impart a tilting of a front wheel to achieve turning. Various embodiments are disclosed.