Cultural characteristics that make rural destinations appealing to visitors could limit local engagement in rural tourism development as well. So, the paper looked at St. Thomas in Jamaica to determine the elements of their culture on which a strong rural tourism product could be built but could also limit local participation in the development of their rural tourism industry. St. Thomas is a rural island community with a rich history steeped in colonialism. Interviews and radio program transcripts as well as notes from a town hall meeting of residents were analyzed. Fifteen elements were identified in this community’s culture that explain their traditional, conservative, close to nature, and spiritual way of life; five were identified as possible drivers of community members’ nonengagement behaviors. A holistic approach to resolving cultural dichotomies in rural tourism communities that would preserve cultural characteristics treasured locally and improve local engagement behaviors was proposed.