Festive leisure provides experiences that can generate intergenerational well-being. The study aimed to examine the festive leisure activities shared by grandparents and grandchildren, and the link with times, spaces, motives, and well-being that these activities bring to both generations. A cross-sectional telematic survey was carried out with 357 grandparents living in the northern part of Spain, who had grandchildren aged between 6 and 12 years. Both a descriptive and inferential analysis was performed. A high proportion of grandparents and grandchildren share festive activities, which occur on weekends and holiday periods. Private spaces, such as bars, cafeterias, and restaurants are the ones chosen for going out to eat or drink, and open public spaces like parks, squares, and streets are dedicated to traditional festivals, and are excellent scenarios for coexistence and intergenerational social interaction. The reasons that drive this practice are associated with the strengthening of emotional ties and family intimacy. Grandparents consider the practice of shared festive leisure to be beneficial for their personal development because they perceive that, thanks to this leisure, they improve their creativity, physical condition, their happiness and fun, the relationship with their grandchildren, and develop new manual and technical skills.