Image plays a crucial role in travel decision-making and in destination selection. Various factors affect the image people hold of destinations, such as the sociodemographics, travel motivations, information search, and destination features like tourism development level. Although tourism generates both positive and negative impacts in territories that can affect visitors’ destination image, the few studies analyzing the influence of the tourism development level on perceptions were carried out among residents. Moreover, the image visitors hold of tourism destinations not only affects their travel plans, but also the decision of others with whom they share their views, including sharing comments on web platforms. Therefore, this study aims to assess the image visitors hold of the Central Region of Portugal (CRP) based on user-generated content (UGC) visible on Tripadvisor, analyze the information most shared, and compare the perceptions on areas with different levels of tourism development. A content analysis of 5095 comments shows that visitors tend to share mainly positive views and information on attractions (cultural and natural), landscape, facilities, and sports/recreational activities. Differences were detected on perceptions of areas according to their tourism development level. Insights are provided on how to maximize potential benefits of the images visitors hold and to improve these perceptions.