A wealth of research suggests that engaging with visual art and visiting art museums is beneficial to flourishing; however, less is known about the potential benefits of digital forms of engagement. An emerging literature provides preliminary evidence of the benefits of digital art engagement, but additional research on mechanisms and potential moderators of the benefits is necessary. The present study examines the impacts of repeated visitation to a virtual art gallery to address three questions: 1) Do well-being, emotion, and immersion differ between those in a digital art gallery versus those reading about art?; 2) Do personality and interest in art influence virtual art gallery visit qualities (i.e., emotion and immersion)?; and 3) Do visit qualities and individual differences predict well-being? A sample of 890 U.S. adults was recruited from Prolific. The findings suggest that: 1) People in a virtual gallery show greater well-being, immersion, and aesthetic emotion than those reading about art; 2) Openness to experience is most strongly linked with visit qualities; and 3) Immersion, positive and aesthetic emotion, extraversion, and neuroticism are associated with well-being. This work suggests that repeated engagement with art in a digital format has benefits and that future research should continue to examine the underlying mechanisms and ways digital art experiences can be best designed to be effective well-being interventions.