Chiral self-assemblies constantly attract great interest because of their potential to provide insight into biological systems and materials science. Herein we report on the efficient preparation of alanine-based chiral metallacycles, rhomboids 1D and 1L and hexagons 2D and 2L using a Pt(II) ← pyridyl directional bonding approach. The metallacycles are subsequently assembled into nanospheres at low concentration, that generate chiral metallogels at high concentration driven by hydrogen bonding, hydrophobic and π-π interactions. The gels consist of microscopic chiral nanofibers with well-defined helicity, as confirmed by circular dichroism (CD) and scanning (SEM) and transmission electron (TEM) microscopies. Given these results, we expect this technique will not only unlock interesting new approaches to understand homochirality in nature but also allow the design of versatile soft materials containing chiral supramolecular cores.