Staying physically active is essential to wellbeing in late life. However, many older adults experience barriers to physical activity. Past research has investigated the development of playful interactive systems to support exercise routines and reduce access barriers. Yet, little research has been done on older adults' needs and preferences regarding technologies that support physical activity. We address this issue through an exploration of older adults' exercise motivations grouped around themes relevant to technology design. We conducted semi-structured interviews with 19 older adults, and followed up with a focus group study of physical trainers and older adults with an active lifestyle. Based on our results, we discuss their conflicting perspectives and challenges on exercise and technology, which leads us to contribute design strategies to support designers as well as researchers wishing to create meaningful and playful fitness applications for older adults.