One of the key aspects in the process of caring for people with diabetes is Therapeutic Education (TE). TE is a teaching process for training patients so that they can self-manage their care plan. Alongside traditional methods of providing educational content, there are now alternative forms of delivery thanks to the implementation of advanced Information Technologies systems such as conversational agents (CAs). In this context, we present the AIDA project: an ensemble of two different CAs intended to provide a TE tool for people with diabetes. The Artificial Intelligence Diabetes Assistant (AIDA) consists of a text-based chatbot and a speech-based dialog system. Their content has been created and validated by a scientific board. AIDA Chatbot—the text-based agent—provides a broad spectrum of information about diabetes, while AIDA Cookbot—the voice-based agent—presents recipes compliant with a diabetic patient’s diet. We provide a thorough description of the development process for both agents, the technology employed and their usage by the general public. AIDA Chatbot and AIDA Cookbot are freely available and they represent the first example of conversational agents in Italian to support diabetes patients, clinicians and caregivers.