We apply principles of positive organizational psychology to a hospitality inn and resort that seeks to focus on “positive hospitality” – the provision of immersive positive education and well-being to guests and employees alike. The Shawnee Institute aspires to serve as a bridge, linking the science of well-being with organizations across the globe. Integrating well-being throughout the Institute’s employees is desired to boost both employee and visitor experiences and distinguish the Institute from other resorts in the region as a destination, and as an employer. We propose an approach to the broad engagement with organizational well-being, discussing the role of cultural change and the needs of both full-time and seasonal employees. We recommend the use of the psychological capital framework to measure and improve well-being across all employees, and provide an implementation plan that includes immersive education for managers, a holistic appreciative inquiry kick-off for all employees, and well-being implementation exercises for on-boarding new employees. This work can assist other organizations, particularly those in the hospitality industry, that seek to improve the well-being of a diverse employee base.