A system of interconnecting luggage includes first and second luggage items. The first luggage item has a handle about an upper end and rolling elements about a base, and is tiltable about a rotational axis of the rolling elements by the handle. The second luggage item also has rolling elements about a base. Each of the first and second luggage items have integral mutual engagement and disengagement elements configured to provide, when the first and second luggage items are mutually engaged, a substantially rigid mechanical connection that maintains the first and second luggage items in relative spatial arrangement such that when the system is in a stable arrangement, the rolling elements of the first and second luggage items contact an underlying planar substrate, and the first luggage item is maintained at a tilt angle relative to the underlying planar substrate.