While empirical evidence primarily establishes leisure travel activities as largely producing short-living rather than long-lasting benefits on well-being, this study explores a promising angle of character strengths, that can potentially guide tourism experience/service design toward greater and more long-lasting well-being benefits. Focusing on a sample of millennials, it aims to reveal 1) what are the weaknesses and unique advantages in current leisure travel offerings with regards to strength deployment, in hope of guiding the future direction of offerings to facilitate strength deployment in leisure travel and augment long-lasting well-being; and 2) the potential influential factors to strength deployment in leisure travel, to inform customized marketing/experience design to fully capitalize on the well-being-boosting power of character strengths. This study also justifies besides the special tourism types, leisure travel in general also has potential unique advantages in benefiting long-term individual well-being.