This chapter explores the demographic profile, motivations, behaviors, challenges, and recommendations of Filipino tourism and hospitality educators who have engaged in leisure while attending a conference and convention. The results have ramifications for higher education institutions (HEI), conference organizers, and tourism and hospitality service providers. The study suggests policy considerations for HEIs to support the educators' active participation in conferences, conventions, and bleisure activities. The results also provide insights for conference organizers as well as tourism and hospitality service providers in customizing and providing quality and cost-friendly services that are tailored to this specific market's needs, expectations, and preferences.