Background: The Pilots for Healthy and Active Ageing (PHArA-ON) project aimsto ensure reality smart and active living for Europe’s ageing population by creating a set of integrated and highly customizable interoperable open platforms with advanced services, devices, and technologies and tools. The aim of the present study was to determine the needs and preferences of older people and their caregivers for improving healthy and active aging and guiding the technological development of thePHArA-ON system. Methods: A pre-structured interview was administered to older adults, informal caregivers and professional caregivers (including social operators) taking part in the piloting sessions. Results: Interviews were carried out in Umana Persone Social Enterprise R&D Network (UP) in Tuscany, and Ospedale Casa SollievodellaSofferenza (CSS) in Apulia. A total of 22 older adults, 22 informal caregivers, 13 professional caregivers and 4 social operators were recruited. A prioritization analysis of services, according to the stakeholder’s needs, has determined two fundamental need categories: Heath Management (i.e., stimulation and monitoring), and Socialisation (i.e., promoting social inclusion). Conclusions: The main scientific contributions to this study are the following: to design and evaluate technology in the context of healthy and active ageing, to acquire relevant knowledge on user needs to develop technologies that can handle the real life situations of older people, obtain useful insights about the attitude and availability of end-users in using technologies in clinical practice, and to provide important guidelines to improve the PHArA-ON system. Specific experimentation stages were also carried out to understand which kind of technology is more acceptable, and to obtain feedback regarding the development priority related to the impact of the proposed services. Research through fruitful and continuous interaction with the different subjects involved in the development process of the system, as well as with stakeholders, enabled the implementation of a platform which could be further and easily integrated and improved.