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The aim of this study was to analyse the association of diet with arterial stiffness and vascular ageing in a Caucasian population with intermediate cardiovascular risk. We recruited 2475 individuals aged 35–75 years with intermediate cardiovascular risk. Brachial-ankle pulse wave velocity (baPWV) was measured using a VaSera VS-1500® device. Vascular ageing was defined in two steps. Step 1: The 20 individuals who presented kidney disease, peripheral arterial disease, or heart failure were classified as early vascular ageing (EVA). Step 2: The individuals with percentiles by age and sex above the 90th percentile of baPWV among the participants of this study were classified as EVA, and the rest of the individuals were classified as non-EVA. The diet of the participants was analysed with two questionnaires: (1) the diet quality index (DQI) questionnaire and (2) the Mediterranean diet (MD) adherence questionnaire. The mean age of the sample was 61.34 ± 7.70 years, and 61.60% were men. Adherence to the MD was 53.30%. The DQI was 54.90%. Of the entire sample, 10.70% (11.15% of the men and 9.95% of the women) were EVA. In the multiple linear regression analysis, for each additional point in the DQI questionnaire, there was a decrease of −0.081 (95%CI (confidence intervals) −0.105–−0.028) in baPWV; in the MD adherence questionnaire, there was a decrease of −0.052 (95%CI −0141–−0.008). When performing the analysis, separated by sex, the association remained significant in men but not in women. In the logistic regression analysis, there was an increase in MD adherence and a decrease in the probability of presenting EVA, both with the DQI questionnaire (OR (odds ratio) = 0.65; 95%CI 0.50–0.84) and with the MD adherence questionnaire (OR = 0.75; 95%CI 0.58–0.97). In the analysis by sex, the association was only maintained in men (with DQI, OR = 0.54; 95%CI 0.37–0.56) (with MD, OR = 0.72; 95%CI 0.52–0.99). The results of this study suggest that a greater score in the DQI and MD adherence questionnaires is associated with lower arterial stiffness and a lower probability of presenting EVA. In the analysis by sex, this association is only observed in men.