The foods and nutrients discussed in this paper are components of dietary patterns that have been associated with lower cardiovascular disease risk. The focus of this review is on the effects of antioxidant foods on vascular health and discussion of their potential mechanisms of action. The foods reviewed include fruits and vegetables, red grapes and red wine, tea, cocoa/chocolate, and olive oil. The primary challenge in studying the cardioprotective components of a dietary pattern is in identifying mechanism(s) of action as well as the bioactive nutrients responsible. In selecting papers for this review, we focused on studies of whole foods and beverages that met the following criteria: 1) they are commonly consumed in typical diets, 2) they appear to have direct antioxidant effects, and 3) they have demonstrated effects on endothelial function in several human studies. The evidence presented herein suggests that dietary consumption of fruits and vegetables, red grapes and red wine, tea, chocolate, and olive oil may improve vascular reactivity, in part, by attenuating the adverse effects of oxidation on endothelial function. Additional research is needed to better understand the mechanism(s) by which antioxidant-rich foods and beverages favorably affect endothelial function and the extent to which this reflects direct antioxidant effects.