Red wine is considered to reduce cardiovascular risk and decrease peripheral systolic and diastolic blood pressure. Central aortic pressures are often more sensitive clinical and prognostic factors than peripheral pressures, while arterial stiffness is an independent prognostic factor for cardiovascular events. Great efforts are being made to find natural sources of improving health. In order to clarify the mechanisms under which a widely used drink, like red wine, is affecting heart and vessels, we aimed to review the available data regarding the effects of red wine on arterial stiffness, wave reflections and central blood pressures. The effect of red wine on central hemodynamics has been poorly explored with divergent results. Possible consequences of acute and long-term intake on arterial stiffness, wave reflections and central pressures are not clear. This might make someone skeptical when suggesting the consumption of a glass of red wine, although its cardioprotective actions (when moderately consumed) are already shown from epidemiological studies.