The present invention provides methods and apparatuses to assess vascular stiffness of a subject, and to assess diabetes or hypertension from the assessment of vascular stiffness. Example embodiments comprise determining arrival at a peripheral site of a blood pressure wave as a function of time relative to the cardiac cycle of the subject at a plurality of measurement conditions, wherein at least two of the conditions are characterized by at least one of: (a) different central transmural pressure, (b) different peripheral transmural pressure; assessing vascular stiffness from the determinations at the plurality of measurement conditions.