A towable baggage item is provided. The towable baggage item includes a body defining a storage compartment, the storage compartment configured to receive and carry objects. The towable baggage item also includes a retractable towing member coupled to the body. Furthermore, the towable baggage item also includes a retractable wheel assembly responsive to a position of the retractable towing member, wherein the retractable wheel assembly comprises at least one wheel and an actuator operatively coupled to each the wheel, wherein the actuator is movable along a first linear axis to extend and retract the wheel along a second linear axis different from the first linear axis.