Abstract Objectives Health behaviours including diet, smoking, alcohol consumption, and physical activity, predict health risks at the population level. We explored health behaviours, barriers to healthy eating and self-rated health among individuals of retirement age. Study design 82 men and 124 women participated in an observational, cross-sectional online survey. Main outcome measures A 14-item Mediterranean diet score (MDPS), perceived barriers to healthy eating (PBHE), self-reported smoking, physical activity habits, and current and prior perceived health status (PHS) were assessed. A health behaviours score (HBS) including smoking, physical activity, body mass index (BMI) and MDPS was created to evaluate associations with PHS. Two-step cluster analysis identified natural groups based on PBHE. Analysis of variance was used to evaluate between group comparisons. Results PBHE number was associated with BMI (r=0.28, P<0.001), age (r=−0.19; P=0.006), and MDPS (r=−0.31; P<0.001). PHBE cluster analysis produced three clusters. Cluster-1 members (busy lifestyle) were significantly younger (57 years), more overweight (28kg/m2), scored lower on MDPS (4.7) and reported more PBHE (7). Cluster-3 members (no characteristic PBHE) were leaner (25kg/m2), reported the lowest number of PBHE (2), and scored higher on HBS (2.7) and MDPS (6.2). Those in PHS categories, bad/fair, good, and very good, reported mean HBS of 2.0, 2.4 and 3.0, respectively (P<0.001). Compared with the previous year, no significant associations between PHS and HBS were observed. Conclusions PBHE clusters were associated with BMI, MDPS and PHS and could be a useful tool to tailor interventions for those of peri-retirement age.