Caffeine is considered to be the most widely consumed pharmacologic substance in the world. Several recent sources of evidence suggest that caffeine, besides its well-established pressor effects, provokes further alterations in arterial stiffness, wave reflections, and especially aortic blood pressures, which are often overlooked. The increasing evidence regarding the prognostic value of the latter cardiovascular factors prompted us to seek additional information concerning the relationship of aortic blood pressures to caffeine consumption. The main purpose of the present review was to evaluate the acute influence of caffeine on arterial stiffness, wave reflections, and central systolic pressures, which are involved in the pathogenesis and prognosis of cardiovascular diseases. Current evidence supports the hypothesis that caffeine influences the cardiovascular system at least acutely, not only through a peripheral blood pressure elevation but also through an increase in arterial stiffness and an enhancement of arterial wave reflections. Moreover, it seems that peripheral pressure measurements might have underestimated caffeine pressor effects, as a significantly greater response is observed in aortic pressures. The mechanisms explaining these effects of caffeine are not always clear, and neither is the role of caffeine in cardiovascular risk. However, it is concluded that strategies aiming at the control of dietary caffeine consumption merit serious consideration.