Previous research investigated the linkage between the Dark Triad traits and subjective well-being, but the factors explaining individual differences in terms of cognitive strategies for achieving happiness remained poorly understood. This study (N = 460) examined the indirect effects of orientations to happiness in the link between dark personality traits and subjective well-being in terms of life satisfaction and positive emotion. Participants completed a questionnaire comprising the Dark Triad Questionnaire, the Orientations to Happiness scale, the Satisfaction with Life scale, and the PANAS. Descriptive statistics, bivariate and partial correlations, and structural equation model were applied to the data. Zero-order and partial correlations showed no significant associations of Machiavellianism and psychopathy with subjective well-being measures, and positive associations of narcissism with the three orientations to happiness and the two dimensions of subjective well-being. Indirect effects indicated that the bright side of narcissism sought the pursuit of the emotional component of SWB by adopting engaging activities. Further studies should replicate our findings.