Nanomedicines for antitumour therapy have been widely studied in recent decades, but only a few have been used in clinical applications. One of the most important reasons is the poor tumour permeability of the nanomedicines. In this three-part review, intravascular, transvascular and extravascular transport were introduced one by one according to their roles in the overall process of nanomedicine transport into tumours. Transportation obstacles, such as elevated interstitial fluid pressure (IFP), abnormal blood vessels, dense tumour extracellular matrix (ECM) and binding site barriers (BSB), were each discussed in the context of the respective transport processes. Furthermore, homologous resolution strategies were summarized on the basis of each transportation obstacle, such as the normalization of blood vessels, regulation of the tumour microenvironment (TME) and application of transformable nanoparticles. At the end of this review, we propose holistic, concrete, and innovative views for better tumour penetration of nanomedicines.