The world ageing problem is prompting new sustainable ways to support elderly people. As such, it is important to promote personalized and intelligent ways to assure the active and healthy ageing of the population. Technological breakthroughs have led to the development of personalized healthcare systems, capable of monitoring and providing feedback on different aspects that can improve the health of the elderly person. Furthermore, defining motivational strategies to persuade the elderly person to be healthier and stay connected to such systems is also fundamental. In this work, a coaching system is presented, especially designed to support elderly people and motivate them to pursue healthier ways of living. To do this, a coaching application is developed using both a cognitive virtual assistant to directly interact with the elderly person and provide feedback on his/her current health condition, and several gamification techniques to motivate the elderly person to stay engaged with the application. Additionally, a set of simulations were performed to validate the proposed system in terms of the support and feedback provided to the user according to his progress, and through interactions with the cognitive assistant.