Social media have emerged as one of the most important tools for firms to engage customers (e.g., Chandrasekaran et al., 2022; Cheng & Edwards, 2015; Lee et al., 2018; Wedel & Kannan, 2016). Within the tourism industry, scholars have investigated the role of social media communication in various contexts, such as online travel information search (Xiang & Gretzel, 2010), sharing travel experiences (So et al., 2018; Wang et al., 2022) and establishing positive customer relationships (Jamshidi et al., 2021). Insights into which social media content makes for generating positive engagement are, however, still largely based on marketers’ intuitions or focusing on message factors of social media posts such as message appeals (e.g., Wang & Lehto, 2020). It also often neglects the importance of the visual component of social media posts, and only a few research have investigated the effects of the image in social media on the travel industry (e.g., Fusté-Forné, 2022). The objective of this research is, therefore, to understand how textual features and image features generate user engagement in social media utilizing cutting-edge transfer learning techniques and to propose how these features should be customized to maximize user engagement for online travel shopping companies. We collect and analyze more than 10,000 Instagram posts from three online travel shopping companies, including Expedia, Priceline, and Kayak. The results from transfer learning algorithms utilizing 24 features, such as the number of people in the image, emotions expressed in the people in the image, hue, and RGB value, successfully predict the level of engagement measured by the number of likes and comments.