Destination images are important information for marketing professionals, local planners, and travel bloggers on social media. The rise of social media has allowed more tourists to share their knowledge, emotions, and experiences from their travels. However, despite the popularity of adapting online narratives to destination images, little or no qualitative analysis has been conducted about island’s sustainable tourism development in the Philippines using information from social media. One type of destination are small islands in the Philippines. The examination is worthwhile inasmuch as the literature has been silent on destination images of top island retreats in the country, although there are many negative images of overcrowded and unsustainable resorts posted by both international and local tourists. Method of this research are using data from 83 travel blogs written from January 2013 to February 2018by visitors of Boracay, the current study extracts underlying themes and subthemes relating to visitors’ overall impressions, cultural exchanges, economic development, and environmental changes. It was determined that tourists are interested in the white beaches, breathtaking landscapes, and varieties of activities offered, such as island-hopping and “mermaiding.” There is also evidence that Boracay continues to face issues concerning its sustainability, such as threats on its unfortunate transportation system, losing its cultural identity, uncontrolled urbanization, and unsustainable solid waste management practices. The findings here are useful for local government, small island tourism planners, and service providers in understanding visitor perceptions of quality and value, which in turn have influenced the island’s competitiveness and sustainability.