This paper presents the results of a series of multi-scale experiments and numerical models concerning the mechanical properties of moso culm functionally graded bamboo structures. On the nano- and microscales, nanoindentation techniques are used to study the local variations in the Young's moduli of moso culm bamboo cross-sections. These are then incorporated into finite element models in which the actual variations in Young's moduli are used to model the deformation and fracture of bamboo during fracture toughness experiments. Similarly, the measured gradations in moduli are incorporated into crack bridging models that predict the toughening observed during resistance curve tests. The implications of the results are discussed for the bio-inspired design of structures that mimic the layered, functionally graded structure of bamboo.