Though solo travel can be an enriching and adventurous experience, staying alone (without social interactions) can sometimes enhance feelings of loneliness and this can be detrimental to a traveler’s mental health. In this paper, we present an AI Travel Buddy. This intelligent system uses real-time facial expression recognition to determine the emotion of travelers at the moment and provides personalized conversational topics based on the detected emotion using the emotion-aware voice assistant. Using the latest CNN architecture for emotion detection, and conversational model for dynamic answers, the AI Travel Buddy is a companion to travelers, delivering emotional support to users on solo trips. The paper describes the technologies used, the system architecture, and its methodology, showing substantial improvement in user engagement emotionally alongside providing overall higher travel satisfaction.